Hydrochloric Acid → Isopropyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 1722410Notes

Reaction equation

HRID 1722410 reaction equation
C[O-].[Na+].CN(C)C([N:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:12]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])=[C:11]([CH3:29])[NH:10][C:9]1=O)=O.Cl.C[S:34](C)=O>CO>[CH3:29][C:11]1[NH:10][C:9](=[S:34])[NH:8][CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:12]=1[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 10942334Sodium MethoxideHCID 148017303-[(Dimethylamino)carbonyl]-1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Product 1

HCID 2748290Isopropyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methoxide in methanol (1.6 ml, 7.5 mmol, 2 eq) was added to a solution of isomer B [described in Example 20, part B] of 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-thioxo-3,5-pyrimidinecarboxylic acid, 5-(1-methylethyl)ester, 3-[(S)-5-methoxycarbonyl)-3-pyrrolidinyl]ester (2.04 g, 3.7 mmol) in methanol (18 ml). The reaction was allowed to stir at room temperature. After 16 hours, the pH was adjusted to 2 with ethereal hydrochloric acid and the mixture was cooled to 0° C. for six hours. The resulting solid was collected by filtration. Three further crops were collected from the mother liquors, which when combined afforded 1.12 g (89%). [α]D =+85° (c=0.5, dimethylsulfoxide).

Workup

  1. temperaturethe mixture was cooled to 0° C. for six hours
  2. filtrationThe resulting solid was collected by filtration
  3. customThree further crops were collected from the mother liquors, which when
  4. customcombined afforded 1.12 g (89%)

Sources & evidence

ORD record
ord-8acab0f156fd4e8ea8620675df81cfb3
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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