e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Journal of the American Chemical Society

Potential Purine Antagonists. IX. Further Studies of Some 4, 6-Disubstituted Pyrazolo [3, 4-d] pyrimidines1

RK Robins

Index: Robins Journal of the American Chemical Society, 1957 , vol. 79, p. 6407,6412

Full Text: HTML

Citation Number: 24

Abstract

A number of new 4, 6-disubstituted pyrazolo [3, 4-d] pyrimidines have been prepared. The successful chlorination of 4, 6-dihpdroxypyrazolo [3, 4-d] pyrimidine(V) to give 4, 6- dichloropyrazolo [3, 4-d] pyrimidine(VI) has provided VI as an intermediate for the preparation of a large number of pyrazolo [3, 4-d] pyrimidines previously unreported. Selective replacement of the chlorine atoms of VI under carefully controlled conditions ...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,6-(dimethylamino)-1,5-dihydro- Structure

4H-Pyrazolo[3,4...

~%

3-dimethylamino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-dimethylamino...

Oxipurinol Structure

~%

3-dimethylamino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-dimethylamino...

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

3-dimethylamino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-dimethylamino...

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-chloro-2,4,8,...

Dimethylamine Structure

~%

3-dimethylamino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-dimethylamino...

4-Hydroxy-6-aminopyrazolo[3,4-d]pyrimidine Structure

4-Hydroxy-6-ami...

~%

6-Amino-1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

6-Amino-1,2-dih...

Oxipurinol Structure

~%

6-Amino-1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

6-Amino-1,2-dih...

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-trien-5-one Structure

3-chloro-2,4,8,...

~%

6-Amino-1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

6-Amino-1,2-dih...

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

6-Amino-1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-thione Structure

6-Amino-1,2-dih...

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-trien-5-one Structure

3-chloro-2,4,8,...

Oxipurinol Structure

~%

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-trien-5-one Structure

3-chloro-2,4,8,...

Oxipurinol Structure

~%

N-methyl-3-methylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

N-methyl-3-meth...

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

N-methyl-3-methylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

N-methyl-3-meth...

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...

~%

N-methyl-3-methylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

N-methyl-3-meth...

5-sulfanylidene-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,6-dien-3-one Structure

5-sulfanylidene...

~%

N-methyl-3-methylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

N-methyl-3-meth...

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-chloro-2,4,8,...

~%

N-methyl-3-methylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

N-methyl-3-meth...

4-methylsulfanyl-1,2-dihydropyrazolo[3,4-d]pyrimidin-6-one Structure

4-methylsulfany...

~%

N-methyl-3-methylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

N-methyl-3-meth...

4-chloro-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-chloro-6-meth...

methylamine Structure

~%

N-methyl-3-methylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

N-methyl-3-meth...

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...

~%

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,6-(methylthio)- Structure

1H-Pyrazolo[3,4...

Oxipurinol Structure

~%

2-[(3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-yl)amino]ethanol Structure

2-[(3-chloro-2,...

2-Aminoethanol Structure

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

2-[(3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-yl)amino]ethanol Structure

2-[(3-chloro-2,...

5-sulfanylidene-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,6-dien-3-one Structure

5-sulfanylidene...

methyl iodide Structure

~%

4-methylsulfanyl-1,2-dihydropyrazolo[3,4-d]pyrimidin-6-one Structure

4-methylsulfany...

Oxipurinol Structure

~%

4,6-dimethoxy-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-dimethoxy-1...

Sodium Methylate Structure

Sodium Methylate

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

4,6-dimethoxy-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-dimethoxy-1...

Oxipurinol Structure

~%

3-chloro-5-ethylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraene Structure

3-chloro-5-ethy...

Ethanethiol Structure

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

3-chloro-5-ethylsulfanyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraene Structure

3-chloro-5-ethy...

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-chloro-2,4,8,...

Oxipurinol Structure

~%

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-chloro-2,4,8,...

Oxipurinol Structure

~%

3-chloro-N-methyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

3-chloro-N-meth...

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

3-chloro-N-methyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

3-chloro-N-meth...

5-sulfanylidene-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,6-dien-3-one Structure

5-sulfanylidene...

~%

3-chloro-N-methyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

3-chloro-N-meth...

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-chloro-2,4,8,...

~%

3-chloro-N-methyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

3-chloro-N-meth...

4-methylsulfanyl-1,2-dihydropyrazolo[3,4-d]pyrimidin-6-one Structure

4-methylsulfany...

~%

3-chloro-N-methyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

3-chloro-N-meth...

6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine Structure

6-Chloro-4-meth...

methylamine Structure

~%

3-chloro-N-methyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

3-chloro-N-meth...

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...

methylamine Structure

~%

3-chloro-N-methyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-5-amine Structure

3-chloro-N-meth...

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-trien-5-one Structure

3-chloro-2,4,8,...

~%

4-Hydroxy-6-aminopyrazolo[3,4-d]pyrimidine Structure

4-Hydroxy-6-ami...

Oxipurinol Structure

~%

4-Hydroxy-6-aminopyrazolo[3,4-d]pyrimidine Structure

4-Hydroxy-6-ami...

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

4-Hydroxy-6-aminopyrazolo[3,4-d]pyrimidine Structure

4-Hydroxy-6-ami...

Oxipurinol Structure

~%

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...

4-methylsulfanyl-1,2-dihydropyrazolo[3,4-d]pyrimidin-6-one Structure

4-methylsulfany...

~%

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...

5-sulfanylidene-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,6-dien-3-one Structure

5-sulfanylidene...

~%

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...

3-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-triene-5-thione Structure

3-chloro-2,4,8,...

methyl iodide Structure

~%

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...

Methyl mercaptan Structure

Methyl mercaptan

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine Structure

4,6-Dichloro-1H...

~%

1H-Pyrazolo[3,4-d]pyrimidine, 6-chloro-4-(methylthio)- Structure

1H-Pyrazolo[3,4...