Benzyl Alcohol → 6-Benzyloxypurine

HRID 1473750Notes

Reaction equation

HRID 1473750 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[NH:14][CH:15]=[N:16]2>O>[CH2:3]([O:10][C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[NH:14][CH:15]=[N:16]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl Alcohol2×HCID 24758Sodium hydrideHCID 53592776-Chloropurine

Product 1

HCID 8536776-Benzyloxypurine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

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. (litt. 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).

Workup

  1. customhas reached room temperature
  2. custom6-Benzyloxypurine was precipitated by the addition of acetic acid (4.6 ml) and diethylether (550 ml)
  3. customThe precipitate was separated by filtration (11.72 g)
  4. customRe-crystallization from ether gave (4.78 g; 65.4%)
  5. custom170-172° C.

Sources & evidence

ORD record
ord-2ab34bf41a164eb49e6b3f413d6d93b8
Source dataset
uspto-grants-2015_04
Patent number
US09017992B2

Reaction notes

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