Methylhydrazine → 2-Methylsulfanyl-pyrimidine-4-carboxylic acid N-methyl-hydrazide

HRID 1838869노트

반응식

HRID 1838869 반응식
[CH3:1][NH:2][NH2:3].[CH3:4][S:5][C:6]1[N:11]=[C:10]([C:12](Cl)=[O:13])[CH:9]=[CH:8][N:7]=1>C(Cl)Cl>[CH3:1][N:2]([C:12]([C:10]1[CH:9]=[CH:8][N:7]=[C:6]([S:5][CH3:4])[N:11]=1)=[O:13])[NH2:3]

참가 물질

4

반응물 2

HCID 6061MethylhydrazineHCID 115429012-Methylsulfanyl-pyrimidine-4-carbonyl chloride

생성물 1

HCID 591204582-Methylsulfanyl-pyrimidine-4-carboxylic acid N-methyl-hydrazide수율 33.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

To a −78° C. stirred solution of methyl hydrazine (17 mL, 318 mmol) in CH2Cl2 (500 mL) is added dropwise a solution of 2-methylsulfanyl-pyrimidine-4-carbonyl chloride (20 g, 106 mmol) in CH2Cl2 (500 mL). The reaction mixture is stirred for 2 hours at −78° C. and then slowly warmed to room temperature. The reaction mixture is concentrated under reduced pressure to give a purple oil. Purification over silica (EtOAc/hexanes 1:1) affords 6.98 g (33% yield) of the desired compound. 1H NMR (300 MHz, CDCl3) δ 8.69-8.64 (m, 1H), 7.35-7.08 (m, 1H), 3.40 (s, 3H), 3.36 (s, 2H), 2.59 (s, 3H); ESI/MS: 199.1 (M+H).

후처리

  1. temperatureslowly warmed to room temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customto give a purple oil
  4. customPurification over silica (EtOAc/hexanes 1:1)

출처 및 근거

ORD 기록
ord-291b76739ee54a64bf992cd327dfecc0
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677337B2

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