Reaction #1005931

Reaction equation

4-methoxybenzene-1-sulfonyl chloride

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

→

product

Yield 64.0%

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

Yield 64.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherresulting in a clear solution
2. 2
   TemperatureAfter cooling to room temperature
3. 3
   OtherThe solvent was evaporated
4. 4
   Otherthe residue was partitioned between ethyl acetate (EtOAc) and brine
5. 5
   DryingThe organic phase was dried over magnesium sulfate (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated

Procedure

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]+).

Source