2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-(4-Morpholino-6-(1-(4-n-methylsulfonylpiperazin-1-yl)ethyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

HRID 1365331Notes

Reaction equation

HRID 1365331 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[S:10][C:9]([CH:11]([N:13]3[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]3)[CH3:12])=[CH:8][C:6]=2[N:7]=1.[NH2:29][C:30]1[N:35]=[CH:34][C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][N:31]=1>>[O:26]1[CH2:27][CH2:28][N:23]([C:4]2[C:5]3[S:10][C:9]([CH:11]([N:13]4[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]4)[CH3:12])=[CH:8][C:6]=3[N:7]=[C:2]([C:33]3[CH:32]=[N:31][C:30]([NH2:29])=[N:35][CH:34]=3)[N:3]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 866184312-Chloro-6-[1-(4-methanesulfonyl-piperazin-1-yl)-ethyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Product 1

HCID 582340665-(4-Morpholino-6-(1-(4-n-methylsulfonylpiperazin-1-yl)ethyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

Procedure

2-Chloro-6-[1-(4-methanesulfonyl-piperazin-1-yl)-ethyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidine was reacted with 2-aminopyrimidine-5-boronic acid pinacol ester in General Procedure A. Purification on silica yielded 300. NMR: (CDCl3): 1.44 (3H, d, J 7.1, Me), 2.52-2.64 (4H, m, CH2), 2.73 (3H, s, Me), 3.21-3.23 (4H, m, CH2), 3.80-3.83 (4H, m, CH2), 3.94-4.06 (5H, m), 5.16 (2H, s, NH2) and 9.20 (2H, s, Ar). MS: (ESI+): MH+=505.20

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-fb6b01154726432d87e5d64eaac3c694
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

Loading…