Реакция #1005931

Уравнение реакции

4-methoxybenzene-1-sulfonyl chloride

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

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product

Выход 64.0%

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

Выход 64.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Другоеresulting in a clear solution
2. 2
   ТемператураAfter cooling to room temperature
3. 3
   ДругоеThe solvent was evaporated
4. 4
   Другоеthe residue was partitioned between ethyl acetate (EtOAc) and brine
5. 5
   СушкаThe organic phase was dried over magnesium sulfate (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated

Методика

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]+).

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