Reacción #1005931

Ecuación de reacción

4-methoxybenzene-1-sulfonyl chloride

4-amino-5-fluoro-pyrimidin-2-ol

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product

Rendimiento 64.0%

4-Amino-5-fluoro-1-(4-methoxyphenylsulfonyl)pyrimidin-2(1H)-one

Rendimiento 64.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroresulting in a clear solution
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   OtroThe solvent was evaporated
4. 4
   Otrothe residue was partitioned between ethyl acetate (EtOAc) and brine
5. 5
   SecadoThe organic phase was dried over magnesium sulfate (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated

Procedimiento

To commercially available 4-amino-5-fluoro-pyrimidin-2-ol (1.0 grams (g), 7.75 millimoles (mmol)) in acetonitrile (CH3CN; 50 milliliters (mL)) was added bis-N,O-trimethylsilylacetamide (BSA; 5.7 mL, 23.3 mmol) and the mixture was heated at 70° C. for 1 hour (h), resulting in a clear solution. After cooling to room temperature, 4-methoxybenzene-1-sulfonyl chloride (1.8 g, 8.5 mmol) was added, and the mixture was stirred for 24 h. The solvent was evaporated and the residue was partitioned between ethyl acetate (EtOAc) and brine. The organic phase was dried over magnesium sulfate (MgSO4), filtered, and evaporated to yield the product as a pale yellow solid (1.48 g, 64%): mp 182-185° C.; 1H NMR (300 MHz, CDCl3) δ 8.40 (br s, 1H), 8.11 (d, J=5.9 Hz, 1H), 8.04-7.98 (m, 2H), 7.02-6.96 (m, 2H), 5.77 (br s, 1H), 3.88 (s, 3H); ESIMS m/z 300 ([M+H]+).

Fuente