반응 #6347

반응 방정식

Phthaloyl dichloride

9-benzyloxyadenine

triethylamine

→

title compound

수율 49.0%

9-Benzyloxy-6-phthalimidopurine

수율 49.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타After 1 hour at room temperature the solvent was removed under reduced pressure
2. 2
   기타the residue partitioned between chloroform (500 ml) and saturated potassium bicarbonate (300 ml)
3. 3
   기타The organic phase was separated
4. 4
   세척washed with water (200 ml), brine (200 ml)
5. 5
   건조dried (MgSO4)
6. 6
   기타evaporated to dryness

실험 절차

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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