Methyl iodide → HCID 178503543, compound

HRID 474715Notes

Reaction equation

HRID 474715 reaction equation
[O-][CH2:2]C.[Na+].[N:5]1[CH:10]=[C:9]([CH2:11][C:12]2[C:13](=[O:19])[NH:14][C:15](=[S:18])[NH:16][CH:17]=2)[CH:8]=[N:7][CH:6]=1.CI>CCO>[CH3:2][S:18][C:15]1[NH:16][CH:17]=[C:12]([CH2:11][C:9]2[CH:10]=[N:5][CH:6]=[N:7][CH:8]=2)[C:13](=[O:19])[N:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 109660395-(Pyrimid-5-ylmethyl)-2-thiouracil

Product 1

HCID 178503543HCID 178503543, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a stirred solution of sodium ethoxide (157.7 mg, 2.32 mmol, 2 eq) in EtOH (5.2 ml) was added 5-pyrimidin-5-ylmethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (270 mg, 1.22 mmol, 1 eq) at rt. After 30 min, the reaction mixture was treated with methyl iodide (190.7 μl, 3.05 mmol, 2.5 eq) and was stirred at rt overnight. Solvent was evaporated and water (1 ml) was added. pH was adjusted ˜4 with 1N HCl and precipitate was formed to give 2-methylsulfanyl-5-pyrimidin-5-ylmethyl-1H-pyrimidin-4-one (196 mg, yield=62.4%, purity=91%). [M+H]+=235.28. 1H NMR (300 MHz; CDCl3) δ/ppm 2.45 (s, 3H), 3.62 (s, 2H), 3.50 (s, 2H), 7.89 (s, 1H), 8.69 (s, 2H), 9.00 (s, 1H)

Workup

  1. customSolvent was evaporated
  2. additionwater (1 ml) was added
  3. customprecipitate was formed

Sources & evidence

ORD record
ord-2d3ef4475cc1497cb0978f7424eb30ee
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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