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

HRID 1958456ノート

反応式

HRID 1958456 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 mixed with 2,4-dichloro-5-trifluoromethylpyrimidine (1.48 mL, 6.8 mmol). The suspension is then refluxed for 100 min with stirring in the oil bath (approx. 130° C.). Once 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 for 100 min
  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-2b5f64ccd23f46e18518e0d88d76e75d
出典データセット
uspto-grants-2013_04
特許番号
US08410126B2

反応ノート

読み込み中…