Methyl iodide → HCID 58739060, compound

HRID 720277Notes

Reaction equation

HRID 720277 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([S:15][CH3:16])[NH:9][C:10](=[O:14])[C:11]=1[O:12][CH3:13])=[O:5])[CH3:2].[H-].[Na+].I[CH3:20]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([S:15][CH3:16])[N:9]([CH3:20])[C:10](=[O:14])[C:11]=1[O:12][CH3:13])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135980894HCID 135980894, compound

Product 1

HCID 58739060HCID 58739060, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methoxy-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.442 g, 1.81 mmol) in dry N,N-dimethylformamide (5 ml) was treated at 10° C. with sodium hydride (0.080 g of a 60% dispersion in mineral oil, 2.0 mmol) and the resulting mixture was stirred for 10 min. Then iodomethane (0.123 ml, 2.0 mmol) was added and the mixture was stirred for another 1 h. The solvent was then evaporated in vacuo and the residue was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 9:1) gave 0.419 g (89% yield) of the title ester as white needles; mp 74.5–76° C. (ether-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.41 (3H, t, J=7.1 Hz, CH3), 2.62 (3H, s, SCH3), 3.55 (3H, s, NCH3), 3.95 (3H, s, OCH3), 4.43 (2H, q, J=7.1 Hz, CH2). Anal. Calcd for C10H14N2O4S: C 46.50, H 5.46; N, 10.85. Found: C 46.73; H, 5.21; N, 10.93.

Workup

  1. stirringthe mixture was stirred for another 1 h
  2. customThe solvent was then evaporated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 9:1)

Sources & evidence

ORD record
ord-744aa7174303423293bc212484ac5d2c
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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