(2-Aminopyrimidin-5-yl)boronic acid → HCID 58234073, compound

HRID 881440Notes

Reaction equation

HRID 881440 reaction equation
Cl[CH:2]([C:18]1[S:26][C:25]2[C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[N:23][CH:22]=[N:21][C:20]=2[CH:19]=1)[N:3]1[CH2:8][CH2:7][CH:6]([S:9]([CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])(=[O:11])=[O:10])[CH2:5][CH2:4]1.[NH2:33][C:34]1[N:39]=[CH:38][C:37](B(O)O)=[CH:36][N:35]=1>>[NH2:33][C:34]1[N:39]=[CH:38][C:37]([C:22]2[N:23]=[C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[C:25]3[S:26][C:18]([CH2:2][N:3]4[CH2:8][CH2:7][CH:6]([S:9]([CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])(=[O:11])=[O:10])[CH2:5][CH2:4]4)=[CH:19][C:20]=3[N:21]=2)=[CH:36][N:35]=1

Participants

3

Reactant 2

HCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 66934059HCID 66934059, compound

Product 1

HCID 58234073HCID 58234073, compound

Procedure

2-[1-(Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)piperidine-4-sulfonyl]-N,N-dimethyl-acetamide was reacted with 2-aminopyrimidine-5-boronic acid in General Procedure A. Purification on silica yielded 309. NMR (CDCl3): 1.98-2.08 (2H, m), 2.18-2.28 (4H, m), 3.04 (3H, s), 3.13-3.17 (2H, m), 3.22 (3H, s), 3.45-3.53 (1H, m), 3.85 (2H, s), 3.90-3.93 (4H, m), 4.03-4.06 (4H, m), 4.08 (2H, s), 5.20 (2H, br), 7.27 (1H, s), 9.30 (2H, s). MS (ESI+): MH+ 561.20 (100%)

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-926446bf06b24be2a3816a18303c7914
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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