Benzyl Bromide → 6-Amino-3-benzyl-2-(methylsulfanyl)pyrimidin-4(3H)-one

HRID 275337Notes

Reaction equation

HRID 275337 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[N:7]=[C:6]([OH:12])[CH:5]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[NH2:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6](=[O:12])[CH:5]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178503503HCID 178503503, compound

Product 1

HCID 200878306-Amino-3-benzyl-2-(methylsulfanyl)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 60% NaH dispersion (1.8 g=45 mmol) in 25 ml DMF at 10° C. add dropwise a solution of 6-amino-2-methylthio-4-hydroxypyrimidine (6.3 g=40 mmol) in 150 ml DMF. When gas evolution subsides, add benzyl bromide (7.5 g=44 mmol). Stir 1.5 hr. at room temperature. Remove DMF and partition the residue between EtOAc and water. Wash the organic layer with water, dry and concentrate. Recrystallize the residue from CH3CN to give the title compound, a white solid. FAB MS: M+1=248.

Workup

  1. customat room temperature
  2. customRemove DMF and partition the residue between EtOAc and water
  3. washWash the organic layer with water
  4. customdry
  5. concentrationconcentrate
  6. customRecrystallize the residue from CH3CN

Sources & evidence

ORD record
ord-e6d595d41f8a4640acf5a34d4f77f567
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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