(2-Aminopyrimidin-5-yl)boronic acid → 5-(4-Morpholino-6-((4-(thiazol-2-ylsulfonyl)piperidin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

HRID 881443Notes

Reaction equation

HRID 881443 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([S:18]([C:21]4[S:22][CH:23]=[CH:24][N:25]=4)(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[NH2:32][C:33]1[N:38]=[CH:37][C:36](B(O)O)=[CH:35][N:34]=1>>[O:29]1[CH2:28][CH2:27][N:26]([C:4]2[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:13][CH2:14][CH:15]([S:18]([C:21]5[S:22][CH:23]=[CH:24][N:25]=5)(=[O:19])=[O:20])[CH2:16][CH2:17]4)=[CH:8][C:6]=3[N:7]=[C:2]([C:36]3[CH:35]=[N:34][C:33]([NH2:32])=[N:38][CH:37]=3)[N:3]=2)[CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 866235432-Chloro-4-morpholin-4-yl-6-[4(thiazole-2-sulfonyl)-piperidin-1-ylmethyl]-thieno[3,2-d]pyrimidine

Product 1

HCID 249485445-(4-Morpholino-6-((4-(thiazol-2-ylsulfonyl)piperidin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

Procedure

2-Chloro-4-morpholin-4-yl-6-[4(thiazole-2-sulfonyl)-piperidin-1-ylmethyl]-thieno[3,2-d]pyrimidine was reacted with 2-aminopyrimidine-5-boronic acid in General Procedure A. Purification on silica yielded 310. NMR (CDCl3): 2.03-2.18 (4H, m), 2.18-2.22 (2H, m), 3.12-3.16 (2H, m), 3.39-3.46 (1H, m), 3.84 (2H, s), 3.90-3.93 (4H, m), 4.03-4.06 (4H, m), 5.20 (2H, br), 7.26 (1H, s), 7.79 (1H, d, J=3.0), 8.11 (1H, d, J=3.0), 9.29 (2H, s). MS (ESI+): MH+ 559.13 (100%)

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-1a9fc552de1747a699e20cd171befd47
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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