(2-Aminopyrimidin-5-yl)boronic acid → HCID 25253996, compound

HRID 1365792Notes

Reaction equation

HRID 1365792 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[N:10]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18](=[O:22])[CH:19]([OH:21])[CH3:20])[CH2:14][CH2:13]3)[S:8][C:6]=2[N:7]=1.[NH2:29][C:30]1[N:35]=[CH:34][C:33](B(O)O)=[CH:32][N:31]=1>>[NH2:29][C:30]1[N:35]=[CH:34][C:33]([C:2]2[N:3]=[C:4]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:5]3[N:10]=[C:9]([CH2:11][N:12]4[CH2:17][CH2:16][N:15]([C:18](=[O:22])[C@@H:19]([OH:21])[CH3:20])[CH2:14][CH2:13]4)[S:8][C:6]=3[N:7]=2)=[CH:32][N:31]=1

Participants

3

Reactant 2

HCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 86630069HCID 86630069, compound

Product 1

HCID 25253996HCID 25253996, compoundYield 24.6%

Procedure

1-[4-(5-Chloro-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidin-2-ylmethyl)-piperazin-1-yl]-2-hydroxy-propan-1-one (100 mg) was reacted with 62 mg of 2-aminopyrimidine-5-boronic acid, pinacol ester via General Procedure A. The product was purified by reverse phase HPLC to yield 28 mg of 108. MS (Q1) 486.2 (M)+.

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a137d97f524d4e668464e215769aea9b
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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