Ammonia → Methyl 6-amino-2-chloropyrimidine-4-carboxylate

HRID 245279

反応式

HRID 245279 の反応式
[NH3:1].[CH3:2][O:3][C:4]([C:6]1[CH:11]=[C:10](Cl)[N:9]=[C:8]([Cl:13])[N:7]=1)=[O:5]>CS(C)=O>[CH3:2][O:3][C:4]([C:6]1[CH:11]=[C:10]([NH2:1])[N:9]=[C:8]([Cl:13])[N:7]=1)=[O:5]

参加物

4

反応物 2

HCID 222Ammonia2 回HCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

生成物 1

HCID 53396493Methyl 6-amino-2-chloropyrimidine-4-carboxylate収率 79%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Ammonia was slowly bubbled through a solution of 2,6-dichloro-pyrimidine-4-carboxylic acid methyl ester (20.0 g, 97 mmol, see H. Gershon, J. Org. Chem. 1962, 27, 3507-3510 for preparation) in DMSO (100 mL) cooled with an ice bath to maintain the temperature below 70° C. When the temperature of the reaction solution began to decline, no additional ammonia was added. When the temperature of the reaction solution reached 44° C., the ice bath was removed. When the temperature of the reaction solution reached 32° C., the reaction mixture was diluted with 200 mL of water and filtered. The filtered product was washed with water, washed with ethyl acetate, and dried under vacuum to provide the title compound (14.4 g, 79% yield) that was used without further purification. Flash chromatography on silica gel yielded an analytically pure sample of the title compound: 1H NMR (DMSO-d6) δ 7.7 (br s, 2H), 7.00 (s, 1H), 3.84 (s, 3H).

後処理

  1. temperaturecooled with an ice bath
  2. temperatureto maintain the temperature below 70° C
  3. customreached 44° C.
  4. customthe ice bath was removed
  5. customreached 32° C.
  6. additionthe reaction mixture was diluted with 200 mL of water
  7. filtrationfiltered
  8. washThe filtered product was washed with water
  9. washwashed with ethyl acetate
  10. customdried under vacuum

出典と根拠

ORDレコード
ord-9d9db4e9deeb485c807ed72b4ad5a9d8
出典データセット
uspto-grants-2014_02
特許番号
US08658791B2

関連ノート

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