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

HRID 1958456노트

반응식

HRID 1958456 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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-2b5f64ccd23f46e18518e0d88d76e75d
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410126B2

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