Methyl iodide → HCID 178499514, compound

HRID 2400131Notes

Reaction equation

HRID 2400131 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([SH:14])[N:3]=1.[CH3:15]I>[OH-].[Na+]>[OH:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178499517HCID 178499517, compound

Product 1

HCID 178499514HCID 178499514, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl (4-hydroxy-6-methyl-2-mercapto-5-pyrimidinyl)-acetate (40 g, 0.19 mol) is dissolved in an aqueous solution of NaOH (8 g in 400 ml H2O). Methyl iodide (29.5 g, 0.2 mol) is added and the mixture is stirred at room temperature for 4 hours. Filtration and drying at high vacuum gives methyl (4-hydroxy-6-methyl-2-methylmercapto-5-pyrimidinyl)-acetate (25.4 g, 60%) as a crystalline solid, having a m.p. of 200° C.

Workup

  1. filtrationFiltration
  2. customdrying at high vacuum

Sources & evidence

ORD record
ord-661eb7235fff40399ec9587eb8efc35a
Source dataset
uspto-grants-1995_09
Patent number
US05453427

Reaction notes

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