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

HRID 653057

Reaction equation

HRID 653057 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-387f7c72c31b4e088cc1806b096bd7b1
Source dataset
uspto-grants-1987_06
Patent number
US04675321

Linked notes

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