Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Reactant | 5-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracil | HCID 21936244 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178494160 | HCID 178494160 | 83.7% |
Reaction Steps
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)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09174968B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-4b9d696b917a4f90a66fd84291c4f8d3 |
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| Source note | uspto-grants-2015_11 |
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