(2-Aminopyrimidin-5-yl)boronic acid → 5-(6-((4-(Methylsulfonylmethylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

HRID 881558Notes

Reaction equation

HRID 881558 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][N:15]([S:18]([CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])(=[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>>[CH3:25][S:22]([CH2:21][S:18]([N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:9]2[S:10][C:5]3[C:4]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[N:3][C:2]([C:36]4[CH:35]=[N:34][C:33]([NH2:32])=[N:38][CH:37]=4)=[N:7][C:6]=3[CH:8]=2)[CH2:13][CH2:14]1)(=[O:20])=[O:19])(=[O:24])=[O:23]

Participants

3

Reactant 2

HCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 872094392-Chloro-6-(4-methanesulfonylmethanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Product 1

HCID 249485435-(6-((4-(Methylsulfonylmethylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

Procedure

2-Chloro-6-(4-methanesulfonylmethanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine was reacted with 2-aminopyrimidine-5-boronic acid in General Procedure A. Purification on silica yielded 416. NMR (CDCl3): 2.67-2.70 (4H, m), 3.24 (3H, s), 3.49-3.54 (4H, m), 3.90 (2H, s), 3.90-3.93 (4H, m), 4.03-4.06 (4H, m), 4.42 (2H, s), 5.24 br s), 7.30 (1H, s), 9.30 (2H, s). MS (ESI+): MH+ 569.17 (100%)

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-c8fc2e4027654091bb2f4bc9db0d4fe2
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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