Methanol → HCID 178503526, compound

HRID 2396678Notes

Reaction equation

HRID 2396678 reaction equation
[OH:1][C:2]1[C:3]2[N:12]=[CH:11][CH:10]=[CH:9][C:4]=2[N:5]=[C:6]([SH:8])[N:7]=1.[CH3:13][O-].[Na+].CO.CI>C(O)(=O)C>[OH:1][C:2]1[C:3]2[N:12]=[CH:11][CH:10]=[CH:9][C:4]=2[N:5]=[C:6]([S:8][CH3:13])[N:7]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 178518555HCID 178518555, compound

Product 1

HCID 178503526HCID 178503526, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 22.1 g (0.123 mot) of 4-hydroxypyrido[3,2-d]pyrimidine-2-thiol, 65 mL of 25 percent sodium methoxide in methanol (0.28 mol), 8.9 mL (20.1 g, 0.142 mol) of methyl iodide, and 500 mL of methanol was prepared and allowed to react at ambient temperature with stirring until the starting material thiol disappeared as determined by high pressure liquid chromatography (HPLC). The mixture was then acidified with acetic acid and the volatile components were removed by evaporation under reduced pressure. The residue was diluted with water and the solids were recovered by filtration, washed with ether, and dried overnight in a vacuum oven. The resultant white powder was the title compound melting at 229°-231° C.

Workup

  1. customwas prepared
  2. customto react at ambient temperature
  3. customthe volatile components were removed by evaporation under reduced pressure
  4. additionThe residue was diluted with water
  5. filtrationthe solids were recovered by filtration
  6. washwashed with ether
  7. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-b763e62674aa4a9b864bb409802d8990
Source dataset
uspto-grants-1996_02
Patent number
US05494887

Reaction notes

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