Potassium Carbonate → 2-Acetylamino-5-(4-aminopyrimidin-2-ylthio)thiazole

HRID 2380639Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7](Br)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[NH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([SH:18])[N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:18][C:14]2[N:13]=[C:12]([NH2:11])[CH:17]=[CH:16][N:15]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-acetylamino-5-bromothiazole (2.2 g), 4-amino-2-mercaptopyrimidine (1.3 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (50 ml) was heated at 90° C. for 2 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The precipitation was collected by filtration, washed with water and dried in vacuo to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 200 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure no give 2-acetylamino-5-(4-aminopyrimidin-2-ylthio)thiazole (1.3 g, yield: 48.7%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was triturated with water
customThe precipitation
filtrationwas collected by filtration
washwashed with water
customdried in vacuo
customto give solid
washeluted with a mixture of chloroform and methanol (10:1)
additionThe fractions containing the objective compound

Sources & evidence

ORD record: ord-ed4f17d1aee6417191d176c210e795e9
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05369107

Reaction notes

Loading…