Methyl iodide → HCID 178503447, compound

HRID 1655588Notes

Reaction equation

HRID 1655588 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([SH:10])[N:4]=1.[CH3:11]I>CO>[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([S:10][CH3:11])[N:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 178429541HCID 178429541, compound

Product 1

HCID 178503447HCID 178503447, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium (1.25 g, 54 mmol, 1.1 equivalents) dissolved in anhydrous methanol (100 mL) was added 4-hydroxy-6-methyl-pyrimidine-2-thiol (7.00 g, 49.2 mmol). The mixture was warmed to ~40° C. and methyl iodide (13.06 mL, 49.2 mmol) was added. The mixture was heated under reflux for 3 hours and then cooled to ambient temperature and allowed to stand overnight. The crystals were filtered, washed with methanol and dried to give 7.10 g (75%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ 2.17 (s, 3H), 2.48 (s, 3H), 5.60 (bs, 1H). MS (DCl/NH3) m/e 157 (M+H)+, 174 (M+H+NH3)+.

Workup

  1. temperatureThe mixture was warmed to ~40° C.
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. filtrationThe crystals were filtered
  5. washwashed with methanol
  6. customdried

Sources & evidence

ORD record
ord-30c52495baa44e0691d9f4c3bde17cc6
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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