Ammonia → 2-Propen-1-yl {3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate

HRID 1961878Notes

Reaction equation

HRID 1961878 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][C:9]=2[C:17]2[C:18]([F:30])=[C:19]([NH:23][C:24](=[O:29])[O:25][CH2:26][CH:27]=[CH2:28])[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1.[NH3:31].CO>>[NH2:31][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][C:9]=2[C:17]2[C:18]([F:30])=[C:19]([NH:23][C:24](=[O:29])[O:25][CH2:26][CH:27]=[CH2:28])[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 579897172-Propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate

Product 1

HCID 579896502-Propen-1-yl {3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate

Procedure

A solution of 2-propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate (535 mg, 1.197 mmol) and ammonia in MeOH 7N (6 ml, 42.0 mmol) was heated to 80° C. for 24 h. The crude reaction mixture was evaporated onto silica gel and chromatographed, (0-15% MeOH in DCM). The title compound was obtained as a yellow foam (233 mg, 41% yield). MS (ESI): 428.1 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. customwas evaporated onto silica gel
  3. customchromatographed

Sources & evidence

ORD record
ord-1899f8aedc4049a094608b11eb250f89
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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