Iodine → 1-Benzhydryl-5-iodo-pyrimidine-2,4-dione

温度

84 °C

5-Iodouracil (0.10 g, 0.42 mmol) was suspended in dry MeCN (2.1 mL) and N,O-bis(trimethylsilyl)acetamide (0.25 mL, 1.05 mmol) was added under nitrogen atmosphere. When the reaction mixture turned clear, bromodiphenyl methane (0.15 g, 0.63 mmol) and a catalytic amount of I2 were added and the reaction mixture was heated at 84° C. for 4 hrs. After cooling to room temperature, the mixture was concentrated under reduced pressure, diluted with EtOAc and washed with water. The aqueous phase was extracted with EtOAc (3×15 mL), the combined organic layers were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 60:40) to afford the title compound (0.15 g, 87%) as white solid. 1H NMR (400 MHz, CDCl3): δ 7.02 (s, 1H), 7.14-7.18 (m, 4H), 7.38-7.45 (m, 6H), 7.46 (s, 1H), 8.58 (s, 1H). MS (ESI) in/Z: 405 [M-H]+.

1. temperatureAfter cooling to room temperature
2. concentrationthe mixture was concentrated under reduced pressure
3. additiondiluted with EtOAc
4. washwashed with water
5. extractionThe aqueous phase was extracted with EtOAc (3×15 mL)
6. washthe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. customthe solvent was removed under reduced pressure
9. customThe crude was purified by column chromatography

ORDレコード

ord-f3e249ab0ca94a429568bf5e4d26a8ff

出典データセット

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09428465B2