3-Fluoro-4-methoxyphenylboronic acid → N*4*-Benzyl-3-(3-fluoro-4-methoxy-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

HRID 1396569Notes

Reaction equation

HRID 1396569 reaction equation
BrC1C2C(=NC(N)=NC=2)N(C)N=1.[CH2:13]([NH:20][C:21]1[N:26]=[C:25]([NH2:27])[N:24]=[C:23]2[N:28]([CH3:32])[N:29]=[C:30](Br)[C:22]=12)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]>>[CH2:13]([NH:20][C:21]1[N:26]=[C:25]([NH2:27])[N:24]=[C:23]2[N:28]([CH3:32])[N:29]=[C:30]([C:36]3[CH:37]=[CH:38][C:39]([O:40][CH3:41])=[C:34]([F:33])[CH:35]=3)[C:22]=12)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 689626923-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamineHCID 86630411N*4*-Benzyl-3-bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine2×

Product 1

HCID 57699545N*4*-Benzyl-3-(3-fluoro-4-methoxy-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

Procedure

This compound is prepared analogously to Example 88 by replacing 3-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Intermediate 3) with N*4*-Benzyl-3-bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (Intermediate 15) and by replacing 2-methoxy-5-trifluoromethylphenylboronic acid with 3-fluoro-4-methoxyphenylboronic acid to afford the title compound.

Workup

  1. customThis compound is prepared analogously to Example 88

Sources & evidence

ORD record
ord-80bedbde13714912842edfc7ede6ad46
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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