Potassium Carbonate → 2-Amino-4-methyl-5-(2-pyrimidinylthio)thiazole

HRID 2380627Notes

Reaction equation

Cl.[NH2:2][C:3]1[S:4][C:5](Br)=[C:6]([CH3:8])[N:7]=1.[SH:10][C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:2][C:3]1[S:4][C:5]([S:10][C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:6]([CH3:8])[N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-amino-5-bromo-4-methylthiazole hydrochloride (1.15 g), 2-mercaptopyrimidine (0.6 g) and potassium carbonate (1.7 g) in N,N-dimethylformamide (20 ml) was heated at 90° C. for 3.5 hours with stirring. The reaction mixture was poured into ice water. The mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1), washed with aqueous saturated sodium chloride and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 100 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 to give 2-amino-4-methyl-5-(2-pyrimidinylthio)thiazole (0.65 g, yield: 58.0%).

Workup

extractionThe mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
washwashed with aqueous saturated sodium chloride
dry with materialdried over magnesium sulfate
concentrationThe solvent was concentrated under reduced pressure
customto give solid
washeluted with a mixture of chloroform and methanol (10:1)
additionThe fractions containing the objective compound
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5e770088d7fa430393c419d7586a246d
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05369107

Reaction notes

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