Reaction #487513

Reaction equation

Sodiumhydride

benzyl alcohol

benzyl alcohol

6-chloropurine

→

6-Benzyloxypurine

Solvents

water

Conditions

Workup

1. 1
   Otherhas reached room temperature
2. 2
   Other6-Benzyloxypurine was precipitated by the addition of acetic acid (4.6 ml) and diethylether (550 ml)
3. 3
   OtherThe precipitate was separated by filtration (11.72 g)
4. 4
   OtherRe-crystallization from ether gave (4.78 g; 65.4%)
5. 5
   OtherMelting point was 175-177° C. (lift. 170-172° C.)[Ramazaeva N., 1989 #473] 1H-NMR (DMSO-d6): 8.53 (1H, s); 8.39 (1H, s); 7.54-7.35 (5H, m); 5.62 (2H, s)

Procedure

Sodiumhydride (60% Dispersion in mineral oil; 3.23 g; 80 mmol) was slowly added to benzyl alcohol (30 ml; 34.7 mmol). After the addition of more benzyl alcohol (10 ml) and 6-chloropurine (5.36 g). The reaction mixture was heated to 100° C. for 4 hours. When the reaction mixture has reached room temperature, water (1 ml) was slowly added. 6-Benzyloxypurine was precipitated by the addition of acetic acid (4.6 ml) and diethylether (550 ml). The precipitate was separated by filtration (11.72 g). Re-crystallization from ether gave (4.78 g; 65.4%). Melting point was 175-177° C. (lift. 170-172° C.)[Ramazaeva N., 1989 #473] 1H-NMR (DMSO-d6): 8.53 (1H, s); 8.39 (1H, s); 7.54-7.35 (5H, m); 5.62 (2H, s).

Source