Methyl acetoacetate → 4(3H)-Pyrimidinone, 6-methyl-2-[2-(trifluoromethyl)phenyl]-

HRID 1725587

반응식

HRID 1725587 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[NH:6].[O-]CC.[Na+].[C:18](OC)(=[O:23])[CH2:19][C:20]([CH3:22])=O>C(O)C>[CH3:22][C:20]1[N:7]=[C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[C:2]([F:12])([F:13])[F:1])[NH:6][C:18](=[O:23])[CH:19]=1

참가 물질

5

반응물 3

HCID 7757Methyl acetoacetateHCID 2723922Sodium ethoxideHCID 32665092-Trifluoromethylbenzamidine

생성물 1

HCID 1358508354(3H)-Pyrimidinone, 6-methyl-2-[2-(trifluoromethyl)phenyl]-수율 50.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-trifluoromethyl-benzamidine (2.13 g, 4 mmol) and sodium ethoxide (0.83 g, 12 mmol) in ethanol (20 mL) was treated with methyl acetoacetate (0.44 mL, 4 mmol) and heated at for 24 hours. The reaction was cooled, concentrated, diluted with water and acidified with 2 N hydrochloric acid. The resulting solution was extracted with ethyl acetate, dried over sodium sulfate and concentrated. Purification by flash chromatography [SiO2, methanol:dichloromethane (3:97)] provided the title compound (0.51 g, 50% yield) as a yellow solid; 1H-NMR (500 MHz, DMSO-d6) δ 12.7 (br s, 1H), 7.9 (m, 1H), 7.8 (m, 2H), 7.7 (m, 1H), 6.3 (s, 1H), 2.21 (s, 3H) ppm; MS (FIA) 255.0 (M+H); Rt (Method A) 2.578 minutes.

후처리

  1. temperatureheated at for 24 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. additiondiluted with water
  5. extractionThe resulting solution was extracted with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by flash chromatography [SiO2, methanol:dichloromethane (3:97)]

출처 및 근거

ORD 기록
ord-422a949d7bad46dfb75b1eb3416d335f
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491730B2

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