(6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methoxy-phenyl)-amine → 6-(2-Aminopyrimidin-5-yl)-n-(3-methoxyphenyl)-1,3-dimethyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 876918Notes

Reaction equation

HRID 876918 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]2=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[N:3]=1.[NH2:22][C:23]1(B2OC(C)(C)C(C)(C)O2)[N:28]=[CH:27][CH:26]=[CH:25][NH:24]1>>[NH2:22][C:23]1[N:28]=[CH:27][C:26]([C:2]2[N:7]=[C:6]3[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]3=[C:4]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[N:3]=2)=[CH:25][N:24]=1

Participants

3

Reactant 2

HCID 58345945(6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methoxy-phenyl)-amineHCID 1317325932-Amino-pyrimidine boronic acid pinacol ester

Product 1

HCID 441815896-(2-Aminopyrimidin-5-yl)-n-(3-methoxyphenyl)-1,3-dimethyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Procedure

(6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methoxy-phenyl)-amine was reacted with 2-amino-pyrimidine boronic acid pinacol ester using General Procedure A to give 118. NMR (CDCl3): 2.74 (3H, s), 3.90 (3H, s), 4.04 (3H, s), 5.28 (2H, br), 6.76 (1H, d), 6.99 (1H, br), 7.35 (1H, d), 7.34 (1H, t), 7.55 (1H, s), 9.38 (2H, s). MS: MH+ 363.22 (25%)

Sources & evidence

ORD record
ord-3aad554a03314508b2c3b18df25f1e26
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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