Methyl pivaloylacetate → 6-tert-Butyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one

HRID 1725590

반응식

HRID 1725590 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[O:19][C:20](=O)[CH2:21][C:22](=O)[C:23]([CH3:26])([CH3:25])[CH3:24]>C(O)C>[C:23]([C:22]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:20](=[O:19])[CH:21]=1)([CH3:26])([CH3:25])[CH3:24]

참가 물질

5

반응물 3

HCID 99597Methyl pivaloylacetateHCID 2723922Sodium ethoxideHCID 32665092-Trifluoromethylbenzamidine

생성물 1

HCID 1361571906-tert-Butyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one수율 32.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-trifluoromethylbenzamidine (1.12 g, 5 mmol), sodium ethoxide (1.02 g, 15 mmol) and 4,4-dimethyl-3-oxo-pentanoic acid methyl ester (0.80 mL, 5 mmol) in ethanol (50 mL) and was heated at reflux for 16 hours. The reaction was cooled, concentrated, diluted with water and acidified with 2 N hydrochloric acid. This solution was extracted with ethyl acetate, dried over sodium sulfate and concentrated. Purification by flash chromatography [SiO2, methanol:dichloromethane (2:98)] provided the title compound (0.48 g, 32% yield) as a yellow solid; 1H-NMR (500 MHz, DMSO-d6) δ12.8 (br s, 1H), 7.89 (d, J=7.5 Hz, 1H), 7.78 (m, 2H), 7.71 (d, J=7.4 Hz, 1H), 6.24 (s, 1H), 1.20 (s, 9H) ppm; LC-MS 297.03 (M+H); Rt (Method A) 3.30 minutes.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. additiondiluted with water
  6. extractionThis solution was extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification by flash chromatography [SiO2, methanol:dichloromethane (2:98)]

출처 및 근거

ORD 기록
ord-aec54b8393784005b76a4656b791942d
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491730B2

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