Stannous chloride dihydrate → 2-Chloro-N4-methylpyrimidine-4,5-diamine

HRID 29821

反応式

HRID 29821 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][N:3]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:10][C:5]1[C:6]([NH:8][CH3:9])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amine

生成物 1

HCID 71471722-Chloro-N4-methylpyrimidine-4,5-diamine収率 54%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-chloro-4-(methylamino)-5-nitropyrimidine (3.76 g, 20 mmol, synthesized from the above procedure), tin(II) chloride dihydrate (18.0 g, 80 mmol) in ethanol (200 mL) is heated at 80° C. After heating for 2 hours, the reaction mixture is cooled to room temperature and concentrated. Ethyl acetate and celite is added to the residue and the mixture is basified with saturated sodium carbonate solution to a pH of 9-10. The mixture is filtered through a pad of celite and washed with ethyl acetate. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. Further purification by column chromatography (silica gel, eluting with ethyl acetate) affords the title compound (1.72 g, 54%).

後処理

  1. temperatureAfter heating for 2 hours
  2. temperaturethe reaction mixture is cooled to room temperature
  3. concentrationconcentrated
  4. additionEthyl acetate and celite is added to the residue
  5. filtrationThe mixture is filtered through a pad of celite
  6. washwashed with ethyl acetate
  7. washThe combined organic extracts are washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customFurther purification
  12. washby column chromatography (silica gel, eluting with ethyl acetate)

出典と根拠

ORDレコード
ord-9d9fd8b0ebb24ca9a0c76a0493c4dc2d
出典データセット
uspto-grants-2008_09
特許番号
US07423038B2

関連ノート

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