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

HRID 653057

반응식

HRID 653057 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-387f7c72c31b4e088cc1806b096bd7b1
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04675321

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