反応 #649924

反応方程式

2-fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Sodium t-butoxide

(S)-2-hexanol

→

title compound

収率 41.2%

2-{[(1S)-1-Methylpentyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

収率 41.2%

溶媒

1,2-dimethoxyethane

反応条件

後処理

1. 1
   その他reaction
2. 2
   その他partitioned between ethyl acetate (100 ml) and water (100 ml)
3. 3
   洗浄The organic phase was washed with water (100 ml)
4. 4
   乾燥saturated brine (50 ml), dried over anhydrous magnesium sulphate
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
8. 8
   その他purified on an aminopropyl (NH2) cartridge (100 g)
9. 9
   洗浄eluting with a 0-100% ethyl acetate in cyclohexane gradient over 40 mins
10. 10
    その他evaporated in vacuo

実験手順

Sodium t-butoxide (4.86 g, 50.6 mmol) was added portionwise to a stirred mixture of (S)-2-hexanol (12 g, 117 mmol) and 1,2-dimethoxyethane (12 ml). The resultant mixture was heated to 50° C. under an atmosphere of nitrogen and then 2-fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (3 g, 12.65 mmol) was added. The resultant mixture was maintained at 50° C. for 20 hours when LCMS indicated complete reaction. The mixture was cooled to room temperature and partitioned between ethyl acetate (100 ml) and water (100 ml). The organic phase was washed with water (100 ml) then saturated brine (50 ml), dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was dissolved in dichloromethane and purified on an aminopropyl (NH2) cartridge (100 g) eluting with a 0-100% ethyl acetate in cyclohexane gradient over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white foam (1.665 g).

出典