2,6-Dichloro-4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenol → 4-[6-Amino-1-methyl-4-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2,6-dichloro-phenol

HRID 1396570Notes

Reaction equation

HRID 1396570 reaction equation
BrC1C2C(=NC(N)=NC=2)N(C)N=1.Br[C:14]1[C:22]2[C:17](=[N:18][C:19]([NH2:32])=[N:20][C:21]=2[NH:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:16]([CH3:33])[N:15]=1.[Cl:34][C:35]1[CH:40]=[C:39](B2OCC(C)(C)CO2)[CH:38]=[C:37]([Cl:49])[C:36]=1[OH:50]>>[NH2:32][C:19]1[N:18]=[C:17]2[N:16]([CH3:33])[N:15]=[C:14]([C:39]3[CH:40]=[C:35]([Cl:34])[C:36]([OH:50])=[C:37]([Cl:49])[CH:38]=3)[C:22]2=[C:21]([NH:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:20]=1

Participants

4

Reactant 3

HCID 513419462,6-Dichloro-4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenolHCID 689626923-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamineHCID 1317321053-Bromo-1-methyl-N*4*-(2-morpholin-4-yl-ethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine2×

Product 1

HCID 1360009024-[6-Amino-1-methyl-4-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2,6-dichloro-phenol

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 3-Bromo-1-methyl-N*4*-(2-morpholin-4-yl-ethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (Intermediate 16) and by replacing 2-methoxy-5-trifluoromethylphenylboronic acid with 2,6-dichloro-4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenol to afford the title compound.

Workup

  1. customThis compound is prepared analogously to Example 88

Sources & evidence

ORD record
ord-34a65cfbc9524df1b33f19f166ef8d4c
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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