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

HRID 2380626ノート

反応式

HRID 2380626 の反応式
Cl.[NH2:2][C:3]1[S:4][C:5](Br)=[CH:6][N:7]=1.[NH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([SH:16])[N:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:2][C:3]1[S:4][C:5]([S:16][C:12]2[N:11]=[C:10]([NH2:9])[CH:15]=[CH:14][N:13]=2)=[CH:6][N:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 221703925-Bromo-1,3-thiazol-2-amine--hydrogen chloride (1/1)HCID 178507909HCID 178507909、化合物

生成物 1

HCID 157291872-Amino-5-(4-aminopyrimidin-2-ylthio)thiazole収率 55.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-amino-5-bromothiazole hydrochloride (2.2 g), 4-amino-2-mercaptopyrimidine (2.2 g) and potassium carbonate (6.5 g) in N,N-dimethylformamide (100 ml) was heated at 90° C. for 2.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and water was added to this residue. The solution 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: 250 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 solid. The solid was triturated with ethanol to give 2-amino-5-(4-aminopyrimidin-2-ylthio)thiazole (1.25 g, yield: 55.6%).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to this residue
  3. extractionThe solution was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  4. washwashed with aqueous saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customto give solid
  8. washeluted with a mixture of chloroform and methanol (10:1)
  9. additionThe fractions containing the objective compound
  10. concentrationconcentrated under reduced pressure
  11. customto give solid
  12. customThe solid was triturated with ethanol

出典と根拠

ORDレコード
ord-2554a99343cc417084acf99b42b06ec0
出典データセット
uspto-grants-1994_11
特許番号
US05369107

反応ノート

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