Methyl chloroformate → Ethyl 3-carbomethoxy-6-methyl-4-phenyl-3,4-dihydropyrimidine-2(1H)one-5-carboxylate

HRID 653057

反応式

HRID 653057 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:8][C:9](=[O:13])[NH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].C[Li].Cl[C:23]([O:25][CH3:26])=[O:24]>O1CCCC1.C(OCC)C>[C:23]([N:8]1[CH:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([CH3:12])[NH:10][C:9]1=[O:13])([O:25][CH3:26])=[O:24]

参加物

6

反応物 3

HCID 6586Methyl chloroformateHCID 220272Ethyl 1,4-dihydro-2-hydroxy-6-methyl-4-phenyl-5-pyrimidinecarboxylateHCID 178418348HCID 178418348、化合物

生成物 1

HCID 13913962Ethyl 3-carbomethoxy-6-methyl-4-phenyl-3,4-dihydropyrimidine-2(1H)one-5-carboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a suspension of ethyl-6-methyl-4-phenyl-3,4-dihydropyrimidine-2(1H)one-5-carboxylate (5.0 mmol) in dry tetrahydrofuran (b 10 mL) under nitrogen at -78° C. was added dropwise 1.5 M methyllithium (11 mmol) in diethyl ether and the reaction mixture allowed to warm to 25° C. After 30 minutes, the reaction mixture was recooled to -78° C. and methyl chloroformate (5.5 mmol) was added. The reaction mixture was allowed to warm to 25° C., then quenched with saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluted with methanol:methylene chloride (5:95) and recrystallized from acetonitrile to give the title product as a solid (mp=179°-180.5° C.).

後処理

  1. customwas recooled to -78° C.
  2. temperatureto warm to 25° C.
  3. customquenched with saturated aqueous ammonium chloride
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluted with methanol:methylene chloride (5:95)
  10. customrecrystallized from acetonitrile

出典と根拠

ORDレコード
ord-387f7c72c31b4e088cc1806b096bd7b1
出典データセット
uspto-grants-1987_06
特許番号
US04675321

関連ノート

読み込み中…