Methyl iodide → HCID 178494160, compound

HRID 705962Notes

Reaction equation

HRID 705962 reaction equation
[O-][CH2:2]C.[Na+].[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][C:14]2[C:15](=[O:21])[NH:16][C:17](=[S:20])[NH:18][CH:19]=2)=[CH:9][N:8]=1.CI>CCO>[CH3:5][O:6][C:7]1[N:8]=[CH:9][C:10]([CH2:13][C:14]2[C:15](=[O:21])[N:16]=[C:17]([S:20][CH3:2])[NH:18][CH:19]=2)=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 219362445-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracil

Product 1

HCID 178494160HCID 178494160, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a stirred solution of sodium ethoxide (1.358 mmol, 2 eq) in EtOH (3 ml) was added 5-(2-methoxy-pyrimidin-5-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.679 mmol, 1 eq) at rt. After 30 min, the reaction mixture was treated with methyl iodide (1.358 mmol, 2 eq) and was stirred at rt overnight. Solvent was evaporated and a crude product was purified on Biotage SP1 Snap Si 10; 15 ml/min in the gradient of EtOAc in Cyclohexane: 0-10% in 30 CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 5-(2-methoxy-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (0.568 mmol, yield=83%, purity=46%). [M+H]+=265.25 1H NMR (300 MHz, DMSO-d6) δ/ppm 2.39 (s, 1H), 3.82-3.87 (m, 3H), 7.75 (s, 1H), 8.47 (s, 2H)

Workup

  1. customSolvent was evaporated
  2. customa crude product was purified on Biotage SP1 Snap Si 10
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-4b9d696b917a4f90a66fd84291c4f8d3
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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