Acetic Acid → 6-Benzyloxypurine
Reaction equation
[Na].Cl[C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2.C(O)(=O)C.[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
Sodium (2.5 g, 109 mmol) was added to distilled benzyl alcohol (45 ml) under nitrogen. 6-Chloropurine (1.0 g, 6.47 mmol) was dissolved in distilled benzyl alcohol (73 ml) and the above solution (27 ml, 64.7 mmol) was added. The reaction was stirred at 100° C. under nitrogen for 5 days. After cooling to room temperature and neutralisation using glacial acetic acid, the solvent was removed in vacuo. Water (70 ml) was added and the product was extracted into ethyl acetate (3×30 ml). The combined organic extracts were dried over MgSO4 and the solvent was removed. After further drying in vacuo, the product was recrystallised from acetone to yield the title compound as a white crystalline solid (0.39 g, 28%), m.p. 173-175° C.; (Found: C, 63.14; H, 4.29; N, 24.80. Calc. for C12H10N4O: C, 63.71; H, 4.46; N, 24.76%); δH (200 MHz, d6-DMSO) 8.480 (1H, s, C(2)H or C(8)H), 8.307 (1H, s, C(2)H or C(8)H), 7.522-7.301 (5H, m, Ph), 5.592 (2H, s, OCH2); m/z 226 (M+, 36%), 197 (8), 120 (35), 91 (Bn+, 100%), 81 (9), 65 (24), 57 (23), 43 (16), 32 (8).
Workup
- distillationto distilled benzyl alcohol (45 ml) under nitrogen
- temperatureAfter cooling to room temperature
- customthe solvent was removed in vacuo
- additionWater (70 ml) was added
- extractionthe product was extracted into ethyl acetate (3×30 ml)
- dry with materialThe combined organic extracts were dried over MgSO4
- customthe solvent was removed
- customAfter further drying in vacuo
- customthe product was recrystallised from acetone
Sources & evidence
- ORD record
- ord-bd91a30e12f049bea0649f62ffb4b63e
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06303618B1
Reaction notes
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