2-Aminopyrimidine-5-boronic acid, pinacol ester → 4-((2-(2-aminopyrimidin-5-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)-N,N-dimethylpiperazine-1-carboxamide

HRID 881273Notes

Reaction equation

HRID 881273 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:27][C:15]3[N:16]=[C:17](Cl)[N:18]=[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:14]=3[CH:13]=2)[CH2:7][CH2:6]1)=[O:4].CC1(C)C(C)(C)OB([C:37]2[CH:38]=[N:39][C:40]([NH2:43])=[N:41][CH:42]=2)O1>>[NH2:43][C:40]1[N:41]=[CH:42][C:37]([C:17]2[N:18]=[C:19]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[C:14]3[CH:13]=[C:12]([CH2:11][N:8]4[CH2:9][CH2:10][N:5]([C:3]([N:2]([CH3:28])[CH3:1])=[O:4])[CH2:6][CH2:7]4)[S:27][C:15]=3[N:16]=2)=[CH:38][N:39]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 568340514-((2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)-N,N-dimethylpiperazine-1-carboxamide

Product 1

HCID 249474144-((2-(2-aminopyrimidin-5-yl)-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)-N,N-dimethylpiperazine-1-carboxamide

Procedure

4-(2-Chloro-4-morpholin-4-yl-thieno[2,3-d]pyrimidin-6-ylmethyl)-piperazine-1-carboxylic acid dimethylamide was reacted with 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine in General Procedure A. Purification on silica yielded 128. NMR (CDCl3): 2.55 (m, 4H, 2×CH2), 2.84 (s, 6H, 2×CH3), 3.32 (m, 4H, 2×CH2), 3.79 (s, 2H, CH2), 3.89-3.91 (m, 4H, 2×CH2), 3.95-3.97 (m, 4H, 2×CH2), 5.24 (sbr, 2H, NH2), 7.14 (s, H, ArH), 9.30 (s, 2H, 2×ArH). MS: (ESI+): MH+=484.31

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-dfb82acd6fcd44b6bfa7aaa9dedd3a3f
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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