Hydrochloric Acid → 1,2,3,4-Tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-3-(3-phenylpropyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1788751Notes

Reaction equation

HRID 1788751 reaction equation
C[O:2][C:3]1[N:4](CCCC2C=CC=CC=2)[CH:5]([CH3:24])[C:6]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1.Cl>CO>[CH3:24][C:5]1[NH:4][C:3](=[O:2])[N:8]([CH2:5][CH2:6][CH2:7][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:6]=1[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 572168171,6-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(3-phenylpropyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Product 1

HCID 138858631,2,3,4-Tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-3-(3-phenylpropyl)-5-pyrimidinecarboxylic acid, 1-methylethyl esterYield 169.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,6-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(3-phenylpropyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (1.96 g. 4.34 mmoles) in methanol (20 ml) was treated with 2.5 N hydrochloric acid (5 ml) and the resulting mixture was allowed to stir at room temperature overnight. A colorless solid precipitated out. Methanol was evaporated and the residue was taken up in ethyl acetate. The solution was washed with water, sodium bicarbonate solution and brine. It was dried over anhydrous magnesium sulfate and evaporated. The residue was crystallized from dichloromethane/isopropyl ether to provide the title compound as a colorless solid (1.61 g), melting point 149.5-151.5° C.

Workup

  1. customA colorless solid precipitated out
  2. customMethanol was evaporated
  3. washThe solution was washed with water, sodium bicarbonate solution and brine
  4. dry with materialIt was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was crystallized from dichloromethane/isopropyl ether

Sources & evidence

ORD record
ord-4b02aacf4a8944cd8a856d38eed02d31
Source dataset
uspto-grants-1987_08
Patent number
US04684655

Reaction notes

Loading…