Potassium Carbonate → 2-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

HRID 388359ノート

反応式

HRID 388359 の反応式
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][C:3]=1[O:18][CH3:19].C([O-])([O-])=O.[K+].[K+].Cl[C:27]1[N:32]=[C:31]([Cl:33])[C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][N:28]=1>O1CCOCC1>[Cl:33][C:31]1[C:30]([C:34]([F:36])([F:35])[F:37])=[CH:29][N:28]=[C:27]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][C:3]=2[O:18][CH3:19])[N:32]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 58200992Benzyl 4-amino-3-methoxybenzoate

生成物 1

HCID 582010032-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
130 °C

実験手順

Benzyl 4-amino-3-methoxybenzoate (1.92 g, 6.8 mmol) and K2CO3 (2.38 g, 17 mmol) are suspended in 4 mL dioxane and then combined with 2,4-dichloro-5-trifluoromethylpyrimidine (1.48 mL, 6.8 mmol). The suspension is then refluxed with stirring in the oil bath (approx. 130° C.) for 100 min. After the reaction has ended the reaction mixture is filtered, the filtrate is concentrated by rotary evaporation and purified by normal phase column chromatography. The product-containing fractions of A-3a (HPLC-MS: tRet.=1.94 min; MS (M−H)+=436) are combined and concentrated by rotary evaporation.

後処理

  1. temperatureThe suspension is then refluxed
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated by rotary evaporation
  4. custompurified by normal phase column chromatography
  5. customThe product-containing fractions of A-3a (HPLC-MS: tRet.=1.94 min; MS (M−H)+=436)
  6. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-f659813d53634300a1ad547bd10b4da2
出典データセット
uspto-grants-2013_02
特許番号
US08377943B2

反応ノート

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