2-Aminopyrimidine-5-boronic acid, pinacol ester → HCID 58233942, compound

HRID 1365149Notes

Reaction equation

HRID 1365149 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].[NH2:30][C:31]1[N:36]=[CH:35][C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33][N:32]=1>>[O:25]1[CH2:26][CH2:27][N:22]([C:19]2[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]=[C:17]([C:34]3[CH:33]=[N:32][C:31]([NH2:30])=[N:36][CH:35]=3)[N:18]=2)[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 86623513HCID 86623513, compound

Product 1

HCID 58233942HCID 58233942, 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-aminopyrimidine-5-boronic acid pinacol ester in General Procedure A. Purification on silica yielded 112. NMR (CDCl3): 2.51-2.55 (4H, m CH2), 2.75 (6H, s, Me), 3.22-3.25 (4H, m, CH2), 3.77 (2H, s, CH2), 3.78-3.82 (4H, m, CH2), 3.94-3.97 (4H, m, CH2), 5.14 (2H, br s, NH2), 7.20 (1H, s, Ar) and 9.20 (2H, s, Ar). MS: (ESI+): MH+=520.34.

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-e8e59327b84a40c9a73d1d1c0fa74c74
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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