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

HRID 253704

反応式

HRID 253704 の反応式
[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]

参加物

5

反応物 3

HCID 99597Methyl pivaloylacetateHCID 2723922Sodium ethoxideHCID 32665092-Trifluoromethylbenzamidine

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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) δ 12.8 (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.

後処理

  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)]

出典と根拠

ORDレコード
ord-eea643965fc04e5f98dae4cbfd3e22de
出典データセット
uspto-grants-2011_01
特許番号
US07872129B2

関連ノート

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