Methyl iodide → HCID 21220636, compound

HRID 1584855Notes

Reaction equation

HRID 1584855 reaction equation
[CH2:1]([C:3]1[C:8]([CH2:9][OH:10])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1)[CH3:2].[CH3:13]I>CC#N>[CH2:1]([C:3]1[C:8]([CH2:9][O:10][CH3:13])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 21220618HCID 21220618, compound

Product 1

HCID 21220636HCID 21220636, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-ethyl-5-hydroxymethyl-2-methylthiopyrimidine (0.63 g, 3.42 mmol), Ag2O (1.6 g, 6.9 mmol) and MeI (1.1 mL, 17.1 mmol) in CH3CN (10 mL) was stirred overnight, filtered and concentrated to give 4-ethyl-5-methoxymethyl-2-methylthiopyrimidine in 98% yield (0.66 g); GC/MS calcd. for C9H14N2OS (M+) 198, found 198. The title compound was then prepared by (a) oxidation of 4-ethyl-5-methoxymethyl-2-methylthiopyrimidine (0.66 g, 3.35 mmol) with mCPBA (1.18 g, 6.85 mmol) as described for Example 67, and (b) reaction with methyl hydrazine (0.36 mL, 6.85 mmol) followed by citraconic anhydride (0.77 g, 6.85 mmol) also described in Example 67; resulting in a yield of 41% (0.40 g) from 4-ethyl-5-methoxymethyl-2-methylthiopyrimidine; 1H NMR (CDCl3) δ 8.14 (s, 1H), 6.43 (s, 1H), 4.29 (s, 2H), 3.53 (s, 3H), 3.36 (s, 3H), 2.68 (m, 2H), 2.14 (s, 3H), 1.13 (m, 3H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-aaac8d1d40074df0a6113621c3a72cc3
Source dataset
uspto-grants-1999_08
Patent number
US05935966

Reaction notes

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