Ethyl Acetoacetate → 6-Methyl-2-(3,4,5-trimethoxyphenylamino)-4(3H)pyrimidinone

HRID 619376

反応式

HRID 619376 の反応式
C[O-].[Na+].C([O:6][C:7](=O)[CH2:8][C:9](=O)[CH3:10])C.[N+]([O-])([O-])=O.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:29][C:30]([NH2:32])=[NH2+:31])[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26]>CO>[CH3:10][C:9]1[N:32]=[C:30]([NH:29][C:21]2[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=2)[NH:31][C:7](=[O:6])[CH:8]=1

参加物

5

反応物 3

HCID 8868Ethyl AcetoacetateHCID 10942334Sodium MethoxideHCID 178419082HCID 178419082、化合物

生成物 1

HCID 1360672746-Methyl-2-(3,4,5-trimethoxyphenylamino)-4(3H)pyrimidinone収率 49%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of sodium methoxide (0.96 g, 1.79 mmol) in methanol was added ethyl-3-oxo-butanoate (0.23 g, 1.79 mmol) and 3,4,5-trimethoxyphenylguanidinium nitrate (0.5 g, 1.79 mmol). The mixture was stirred at reflux for 17 h. The reaction mixture was cooled to room temperature and evaporated in vacuo to give a dark grey solid. Recrystallisation from ethanol gave the title compound (0.25 g, 49%) as a light grey solid, m.p. 228-230° (dec). δH (d6DMSO) 2.12 (3H, s), 3.61 (3H, s), 3.74 (6H, s), 5.69 (1H, s), 7.02 (2H, s), 8.70 (1H, br s) and 10.47 (1H, br s).

後処理

  1. temperatureat reflux for 17 h
  2. customevaporated in vacuo
  3. customto give a dark grey solid
  4. customRecrystallisation from ethanol

出典と根拠

ORDレコード
ord-1b0da2ee48d040c7bcd2d8820ff7cc5b
出典データセット
uspto-grants-1999_09
特許番号
US05958935

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