Dimethyl Sulfate → HCID 18756205, compound

HRID 433934Notes

Reaction equation

HRID 433934 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([SH:9])[CH2:4][N:3]=1.[OH-].[Na+].S(OC)(O[CH3:16])(=O)=O>O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([S:9][CH3:16])[CH2:4][N:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 18756213HCID 18756213, compound

Product 1

HCID 18756205HCID 18756205, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 g (107 mmol) of 4,6-dimethyl-1-mercaptopyrimidine and 5.14 g of NaOH were dissolved in 175 ml of water. 12 ml (128 mmol) of dimethyl sulfate were added dropwise to this mixture at room temperature over the course of 10 minutes. After 1 hour, the aqueous phase was extracted 3 times with ether and dried over magnesium sulfate, and the solvent was distilled off. 15.9 g (97%) of crude product were isolated. 1H-NMR (270 MHz): 6.7 ppm (1H, s), 2.5 (3H, s), 2.3 (6H, s).

Workup

  1. extractionthe aqueous phase was extracted 3 times with ether
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-10775c48414a4f5ab21a4438998f9355
Source dataset
uspto-grants-2003_12
Patent number
US06670367B1

Reaction notes

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