2-Aminopyrimidine-5-boronic acid, pinacol ester → HCID 58234035, compound

HRID 390871Notes

Reaction equation

HRID 390871 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:39]2[CH:40]=[N:41][C:42]([NH2:45])=[N:43][CH:44]=2)O1>>[O:28]1[CH2:27][CH2:26][N:25]([C:4]2[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]4)=[CH:8][C:6]=3[N:7]=[C:2]([C:39]3[CH:40]=[N:41][C:42]([NH2:45])=[N:43][CH:44]=3)[N:3]=2)[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 57494058Tert-butyl 4-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 58234035HCID 58234035, compound

Procedure

2-Chloro-6-((4-Boc-piperazin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidine (200 mg) was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine 7 following General Procedure A followed by Boc removal with 1N HCl in dioxane to generate 159 after reversed phase HPLC purification. MS (Q1) 413 (M)+.

Workup

  1. customfollowed by Boc removal with 1N HCl in dioxane
  2. customafter reversed phase HPLC purification

Sources & evidence

ORD record
ord-81214e1d72704a7b9c1f45818d9a6d98
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

Loading…