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

HRID 2110663

反応式

HRID 2110663 の反応式
[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

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27340942-(2-Chloro-6-fluorophenyl)ethan-1-amine2 回HCID 576361374-Chloro-6-(6-methoxy-pyridin-3-yl)-2-methylsulfanyl-pyrimidine2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 84541-Methylpyrrolidine溶媒

反応条件

温度
175 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-07b927087b194c79b4bd062a3d27ea5f
出典データセット
uspto-grants-2009_04
特許番号
US07517889B2

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