Sodium Carbonate → [2-(2-Chloro-6-fluoro-phenyl)-ethyl]-[6-(6-methoxy-pyridin-3-yl)-2-methylsulfanyl-pyrimidin-4-yl]-amine

HRID 2110663

반응식

HRID 2110663 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][NH2:11].C([O-])([O-])=O.[Na+].[Na+].Cl[C:19]1[CH:24]=[C:23]([C:25]2[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[N:22]=[C:21]([S:33][CH3:34])[N:20]=1>CN1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][NH:11][C:19]1[CH:24]=[C:23]([C:25]2[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[N:22]=[C:21]([S:33][CH3:34])[N:20]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27340942-(2-Chloro-6-fluorophenyl)ethan-1-amine2회HCID 576361374-Chloro-6-(6-methoxy-pyridin-3-yl)-2-methylsulfanyl-pyrimidine2회

생성물 1

HCID 11553210[2-(2-Chloro-6-fluoro-phenyl)-ethyl]-[6-(6-methoxy-pyridin-3-yl)-2-methylsulfanyl-pyrimidin-4-yl]-amine수율 94.5%

시약·촉매·용매 2

HCID 962Water용매HCID 84541-Methylpyrrolidine용매

반응 조건

온도
175 °C

실험 절차

A mixture of 2-(2-chloro-6-fluoro-phenyl)-ethylamine [1.02 g, 5.88 mmol, Intermediate (23)], Na2CO3 (1.65 g, 19.6 mmol), and 4-chloro-6-(6-methoxy-pyridin-3-yl)-2-methylsulfanyl-pyrimidine [1.05 g, 3.92 mmol, Intermediate (38)] in N-methyl pyrrolidine (10 mL), is heated to 175° C. for 3 hours. The reaction mixture is diluted with water, and extracted with ethyl acetate. The extracts are washed with water, dried over magnesium sulfate, filtered, and concentrated. The residue is subjected to short-path chromatography on silica gel eluting with EtOAc to afford [2-(2-chloro-6-fluoro-phenyl)-ethyl]-[6-(6-methoxy-pyridin-3-yl)-2-methylsulfanyl-pyrimidin-4-yl]-amine [1.5 g, Example 30]. LCMS: RT=3.37 minutes, MS: 405 (M+H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extracts are washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-07b927087b194c79b4bd062a3d27ea5f
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517889B2

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