Methyl iodide → HCID 178503543, compound

HRID 705953Notes

Reaction equation

HRID 705953 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-1e60302f83d54f68bb1db978ba925bd1
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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