(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 24947049, compound

HRID 390832Notes

Reaction equation

HRID 390832 reaction equation
[CH3:1][N:2]([CH3:29])[S:3]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[S:21][C:20]3[C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[N:18][C:17](Cl)=[N:16][C:15]=3[CH:14]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4].[CH3:30][O:31][C:32]1[N:37]=[C:36]([O:38][CH3:39])[C:35](B(O)O)=[CH:34][N:33]=1>>[CH3:30][O:31][C:32]1[N:37]=[C:36]([O:38][CH3:39])[C:35]([C:17]2[N:18]=[C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:20]3[S:21][C:13]([CH2:12][N:9]4[CH2:10][CH2:11][N:6]([S:3]([N:2]([CH3:29])[CH3:1])(=[O:5])=[O:4])[CH2:7][CH2:8]4)=[CH:14][C:15]=3[N:16]=2)=[CH:34][N:33]=1

Participants

3

Reactant 2

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 86623513HCID 86623513, compound

Product 1

HCID 24947049HCID 24947049, compound

Procedure

4-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazine-1-sulfonic acid dimethylamide (Example 28) was reacted with 2,4-dimethoxypyrimidine-5-boronic acid in General Procedure A. Purification on silica yielded 113. NMR (CDCl3): 2.50-2.53 (4H, m, CH2), 2.75 (6H, s, Me), 3.21-3.24 (4H, m, CH2), 3.68-3.71 (6H, m, CH2), 3.94-3.98 (4H, m, CH2), 4.01 (3H, s, Me), 4.04 (3H, s, Me), 7.20 (1H, s, Ar) and 8.87 (1H, s, Ar). MS: (ESI+): MH+=565.44

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-37f17c8e9fc249fdb4738ff8739e1704
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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