Hydrochloric Acid → 1,2,3,4-Tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-3-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1722402Notes

Reaction equation

HRID 1722402 reaction equation
C[O:2][C:3]1[N:4]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:6]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[C:7]([CH3:9])[N:8]=1.CO.Cl>O1CCCC1>[CH3:9][C:7]1[NH:8][C:3](=[O:2])[N:4]([C:25]([NH:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[CH:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:6]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 148551061,6-Dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-1-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Product 1

HCID 148017361,2,3,4-Tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-3-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,6-dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-1-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester (3.00 g, 6.45 mmol) in tetrahydrofuran (50 ml)/methanol (25 ml) was treated with 1 N hydrochloric acid (6.0 ml, pH 1) and stirred at room temperature for 1 hour. The reaction was quenched with saturated sodium bicarbonate and partially evaporated. The residue was partitioned between chloroform and water. The organic phase was washed with saturated sodium chloride, dried (magnesium sulfate) and evaporated. The residue was crystallized from dichloromethane/isopropyl ether. The solids which precipitated were recrystallized to give the title compound as a colorless electrostatic solid (1.84 g), melting point 184°-185° C. TLC (5% ethyl acetate/dichloromethane) single spot, Rf =0.39.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate
  2. custompartially evaporated
  3. customThe residue was partitioned between chloroform and water
  4. washThe organic phase was washed with saturated sodium chloride
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residue was crystallized from dichloromethane/isopropyl ether
  8. customThe solids which precipitated
  9. customwere recrystallized

Sources & evidence

ORD record
ord-9e4f5aab06cb41e89e2f2709beac330e
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

Loading…