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

HRID 253701

反応式

HRID 253701 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: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

参加物

5

反応物 3

HCID 7757Methyl acetoacetateHCID 2723922Sodium ethoxideHCID 32665092-Trifluoromethylbenzamidine

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)]

出典と根拠

ORDレコード
ord-498c478e0ede464c8788cf90134de9c7
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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