Acetic Acid → O-(6)-Methylguanine

温度

50 °C

To a solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine (0.25 g, 0.61 mmol) in methanol (5 ml), was added sodium methoxide solution (30 wt % in methanol; 0.5 ml, 2.62 mmol). The mixture was stirred and heated at 50° C. for 4 hours. After cooling to ambient temperature, 80% aqueous acetic acid (0.5 ml) was added to give a solution of pH6. The solution was evaporated to dryness and the residue partitioned between dichloromethane (10 ml) and aqueous sodium bicarbonate solution (10 ml). The aqueous phase was washed with dichloromethane (2×10 ml), the combined organic extracts dried (magnesium sulphate), and evaporated to dryness under reduced pressure. The residue obtained was chromatographed on silica gel (eluant dichloromethane: methanol 90:10) to give a 2-amino-6-methoxypurine derivative (0.20 g) which was used without any further purification. The chromatographed material (0.20 g) was dissolved in dichloromethane (2 ml), trimethylsilyl bromide (0.7 ml, 5.3 mmol) added, and the solution left at ambient temperature for 2 days. The solvent was evaporated under reduced pressure and the residue obtained co-evaporated with methanol (×2) to leave a white solid which crystallised from hot water giving the title compound as a white solid (0.105 g, 56%) m.p. 275°-278° C., identical in all respects with the compound obtained in Method A.

1. temperatureAfter cooling to ambient temperature
2. customto give a solution of pH6
3. customThe solution was evaporated to dryness
4. customthe residue partitioned between dichloromethane (10 ml) and aqueous sodium bicarbonate solution (10 ml)
5. washThe aqueous phase was washed with dichloromethane (2×10 ml)
6. dry with materialthe combined organic extracts dried (magnesium sulphate)
7. customevaporated to dryness under reduced pressure
8. customThe residue obtained
9. customwas chromatographed on silica gel (eluant dichloromethane: methanol 90:10)

ORDレコード

ord-0650dbba12e64ab9a33df5f5a561be3d

出典データセット

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05247085