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

HRID 1656988Notes

Reaction equation

HRID 1656988 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 189547282-Amino-5-bromo-4-methyl-1,3-thiazole hydrochlorideHCID 178418793HCID 178418793, compound

Product 1

HCID 157291882-Amino-4-methyl-5-(2-pyrimidinylthio)thiazoleYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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%). mp: 165°-170° C. (dec.) IR (Nujol): 3300, 3175, 1630, 1555, 1490, 1320 cm-1

Workup

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

Sources & evidence

ORD record
ord-b7fc3d6e311d4898a112258e82979214
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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