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

Aryl coupling reactions of pyrazolo [3, 4-d] pyrimidin-4-yl radicals

JB Press, NH Eudy, GO Morton

Index: Press, Jeffery B.; Eudy, Nancy H.; Morton, George O. Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4605 - 4611

Full Text: HTML

Citation Number: 8

Abstract

3 forward synthesis of 4 could be envisioned as a one-step Gomberg-Bachmann-Hey aryl coupling reaction3 between readily available 4-aminopyrazolo [3, 4-d] pyrimidines (5) 4 and a variety of aromatic solvents. This method would allow for specific control of the site for arylation as well as for the preparation of numerous analogues from only a few common radical intermediates. A similar approach to the preparation of 6, the purine analogue of 4, ...

7,9-dimethyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-5-amine Structure

7,9-dimethyl-2,...

~6%

1,3-Dimethyl-1,5-dihydro-4H-pyrazolo-[3,4-d]pyrimidin-4-one Structure

1,3-Dimethyl-1,...

7,9-dimethyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

7,9-dimethyl-2,...

1,3-dimethyl-4-(pentyloxy)-1H-pyrazolo(3,4-d)pyrimidine Structure

1,3-dimethyl-4-...

Detail

7,9-dimethyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-5-amine Structure

7,9-dimethyl-2,...

Toluene Structure

~5%

1,3-Dimethyl-1,5-dihydro-4H-pyrazolo-[3,4-d]pyrimidin-4-one Structure

1,3-Dimethyl-1,...

7,9-dimethyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraene Structure

7,9-dimethyl-2,...

Detail

PP3 Structure

Anisole Structure

~0%

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-phenyl- Structure

4H-Pyrazolo[3,4...

4-(4-methoxyphenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-methoxyphe...

Detail

PP3 Structure

Anisole Structure

~0%

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-phenyl- Structure

4H-Pyrazolo[3,4...

4-(4-methoxyphenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-methoxyphe...

Detail

PP3 Structure

~0%

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-phenyl- Structure

4H-Pyrazolo[3,4...

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

Detail

PP3 Structure

Chlorobenzene Structure

~0%

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-phenyl- Structure

4H-Pyrazolo[3,4...

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

Detail

PP3 Structure

benzene Structure

~20%

1,4-diphenylpyrazolo[3,4-d]pyrimidine Structure

1,4-diphenylpyr...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-phenyl- Structure

4H-Pyrazolo[3,4...

PP3 Structure

~0%

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-phenyl- Structure

4H-Pyrazolo[3,4...

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

Detail

PP3 Structure

Chlorobenzene Structure

~0%

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-phenyl- Structure

4H-Pyrazolo[3,4...

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

Detail

N/A Structure

~17%

3-methyl-1-phenylpyrazolo[3,4-d]pyrimidine Structure

3-methyl-1-phen...

3-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one Structure

3-methyl-1-phen...

5-(3-methyl-1-phenyl-4-pyrazolyl)-3-phenyl-1,2,4-oxadiazole Structure

5-(3-methyl-1-p...

Detail

N/A Structure

Anisole Structure

~11%

3-methyl-1-phenylpyrazolo[3,4-d]pyrimidine Structure

3-methyl-1-phen...

3-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one Structure

3-methyl-1-phen...

Detail

1-Methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine Structure

1-Methyl-1H-pyr...

~59%

1-methyl-4-phenylpyrazolo[3,4-d]pyrimidine Structure

1-methyl-4-phen...

1-METHYL-1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE Structure

1-METHYL-1,5-DI...

1-methyl-4-(pentyloxy)-1H-pyrazolo(3,4-d)pyrimidine Structure

1-methyl-4-(pen...

1-Methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine Structure

1-Methyl-1H-pyr...

benzene Structure

~14%

1-methyl-4-phenylpyrazolo[3,4-d]pyrimidine Structure

1-methyl-4-phen...

1-METHYL-1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE Structure

1-METHYL-1,5-DI...

Detail

7,9-dimethyl-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-5-amine Structure

7,9-dimethyl-2,...

Toluene Structure

~22%

1,3-Dimethyl-1,5-dihydro-4H-pyrazolo-[3,4-d]pyrimidin-4-one Structure

1,3-Dimethyl-1,...

1,3-dimethyl-4-(p-methylphenyl)pyrazolo(3,4-d)pyrimidine Structure

1,3-dimethyl-4-...

Detail

1-Methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine Structure

1-Methyl-1H-pyr...

Chlorobenzene Structure

~41%

1-METHYL-1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE Structure

1-METHYL-1,5-DI...

1-methyl-4-(m-chlorophenyl)pyrazolo(3,4-d)pyrimidine Structure

1-methyl-4-(m-c...

Detail

1-Methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine Structure

1-Methyl-1H-pyr...

Anisole Structure

~43%

1-METHYL-1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE Structure

1-METHYL-1,5-DI...

1-methyl-4-(m-anisyl)pyrazolo(3,4-d)pyrimidine Structure

1-methyl-4-(m-a...

Detail

1-Methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine Structure

1-Methyl-1H-pyr...

Toluene Structure

~34%

1-METHYL-1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE Structure

1-METHYL-1,5-DI...

1-methyl-4-(m-methylphenyl)pyrazolo(3,4-d)pyrimidine Structure

1-methyl-4-(m-m...

Detail