Benzyl Bromide → HCID 13975872, compound

HRID 568337Notes

Reaction equation

HRID 568337 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[S:8])[NH:5][CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC(C)=O>[CH3:1][C:2]1[NH:7][C:6]([S:8][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:5][CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2787683ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 13975872HCID 13975872, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-thioxo-5-pyrimidinecarboxylic acid, ethyl ester (400 mg., 1.24 mmole), potassium carbonate (270 mg., 2.0 mmole) and benzyl bromide (240 mg., 1.4 mmole) in acetone (7.0 ml.) is stirred at room temperature overnight. The solid is filtered off and the filtrate is diluted with ethyl acetate. The solution is washed with water and brine, and is dried over anhydrous magnesium sulfate. Evaporation of the solvent provides a light yellow solid which is triturated with isopropyl ether and filtered off to give 370 mg. of product. This material is combined with product from another run (150 mg.) and recrystallized from isopropyl etherdichloromethane to give 1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2-[(phenylmethyl)thio]-5-pyrimidinecarboxylic acid, ethyl ester as light yellow crystals; m.p. 129°-130°. TLC (silica gel; ethyl acetate:hexane, 40:60) Rf =0.39.

Workup

  1. filtrationThe solid is filtered off
  2. additionthe filtrate is diluted with ethyl acetate
  3. washThe solution is washed with water and brine
  4. dry with materialis dried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customprovides a light yellow solid which
  7. customis triturated with isopropyl ether
  8. filtrationfiltered off
  9. customto give 370 mg
  10. customrecrystallized from isopropyl etherdichloromethane

Sources & evidence

ORD record
ord-af0593461da641f79cea7dca0b15a990
Source dataset
uspto-grants-1988_03
Patent number
US04728652

Reaction notes

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