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

HRID 1722397Notes

Reaction equation

HRID 1722397 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([N:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[C:8]([CH3:26])[N:7]=[C:6]1[O:27]C)=[O:4].Cl>O1CCCC1.CO>[CH3:29][N:2]([CH3:1])[C:3]([N:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([O:22][CH:23]([CH3:24])[CH3:25])=[O:21])=[C:8]([CH3:26])[NH:7][C:6]1=[O:27])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 142570701-[(Dimethylamino)carbonyl]-1,6-dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Product 1

HCID 148017303-[(Dimethylamino)carbonyl]-1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methylethyl esterYield 70.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of crude 1-[(dimethylamino)carbonyl]-1,6-dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (2.27 g), in tetrahydrofuran/methanol (20 ml each) was treated with 5N hydrochloric acid (3.0 ml, pH1) and stirred at room temperature for 1.0 hour. The reaction was then evaporated and partitioned between ethyl acetate and water. The organic phase was washed with saturated sodium chloride, dried (magnesium sulfate), and evaporated. The residue was crystallized from dichloromethane/isopropyl ether to give the title compound as colorless crystals (1.55 g), melting point 165°-166° C.

Workup

  1. customThe reaction was then evaporated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with saturated sodium chloride
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated
  6. customThe residue was crystallized from dichloromethane/isopropyl ether

Sources & evidence

ORD record
ord-7e0e36ef37f4426fa6f48cbad00c7cd1
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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