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

HRID 388359노트

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HRID 388359 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f659813d53634300a1ad547bd10b4da2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377943B2

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