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

HRID 495029

반응식

HRID 495029 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9](S(C)(=O)=O)[N:8]=[C:7]([Cl:15])[N:6]=1)=[O:4].[NH3:16]>O1CCOCC1.CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:16])[N:8]=[C:7]([Cl:15])[N:6]=1)=[O:4]

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 84031284Methyl 2-chloro-6-(methylsulfonyl)pyrimidine-4-carboxylate

생성물 1

HCID 53396493Methyl 6-amino-2-chloropyrimidine-4-carboxylate수율 85%

시약·촉매·용매 2

HCID 887Methanol용매HCID 312751,4-Dioxane용매

실험 절차

2-Chloro-6-methanesulfonylpyrimidine-4-carboxylic acid methyl ester (3.7 g, 14.75 mmol) was dissolved in dioxane and 7N ammonia in methanol was added. The reaction mixture was stirred at room temperature for 3 hours, concentrated under vacuum, and the residue partitioned between ethyl acetate and water. The organic phase was dried and concentrated. The product was purified by column chromatography to provide 6-amino-2-chloropyrimidine-4-carboxylic acid methyl ester (2.35 g, 85% yield): 1H NMR (DMSO-d6): δ 7.6 (br s, 1H), 7.00 (s, 1H), 3.84 (s, 3H), 3.33 (s, 3H).

후처리

  1. concentrationconcentrated under vacuum
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography

출처 및 근거

ORD 기록
ord-66fb0aa808b34c818b7117d066569607
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538214B2

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