Реакция #6347

Уравнение реакции

Phthaloyl dichloride

9-benzyloxyadenine

triethylamine

→

title compound

Выход 49.0%

9-Benzyloxy-6-phthalimidopurine

Выход 49.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ДругоеAfter 1 hour at room temperature the solvent was removed under reduced pressure
2. 2
   Другоеthe residue partitioned between chloroform (500 ml) and saturated potassium bicarbonate (300 ml)
3. 3
   ДругоеThe organic phase was separated
4. 4
   Промывкаwashed with water (200 ml), brine (200 ml)
5. 5
   Сушкаdried (MgSO4)
6. 6
   Другоеevaporated to dryness

Методика

Phthaloyl dichloride (13.35 g; 92.2 mmol) was added to a cooled solution of 9-benzyloxyadenine (14.9 g, 61.5 mmol), 4-dimethylaminopyridine (1.5 g, 12.3 mmol) and triethylamine (25.7 ml, 184.4 mmol) in tetrahydrofuran (200 ml). After 1 hour at room temperature the solvent was removed under reduced pressure and the residue partitioned between chloroform (500 ml) and saturated potassium bicarbonate (300 ml). The organic phase was separated, washed with water (200 ml), brine (200 ml), dried (MgSO4) and evaporated to dryness. Column chromatography on silica gel eluting with chloroformmethanol (100:1) afforded the title compound (11.20 g, 49%). IR: νmax (KBr) 3070, 1800, 1740, 1730, 1605, 1585, 1450 and 1410 cm-1 ; 1H NMR δH [(CD3)2SO] 5.70(2H, s, CH2Ph), 7.55(5H, s, CH2Ph), 8.20(4H, s, Ar), 8.95(1H, s, H-2), 9.25(1H, s, H-8). Found: C, 64.71; H, 3.78; N, 18.85%; m/z 371.1025. C20H13N5O3 requires: C, 64.68; H, 3.54; N, 18.86%; m/e 371.1018.

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