Benzyl Alcohol → 6-Benzyloxypurine

HRID 1034601Notes

Reaction equation

HRID 1034601 reaction equation
[H-].[Na+].[CH:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=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>[CH2:9]([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:6]1[CH:7]=[CH:8][CH:3]=[CH:4][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 Benzylalkohol (30 ml; 34.7 mmol). After the addition of more benzylalkohol (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). Recrystallization from ether gave (4.78 g; 65.4%). Melting point 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. customRecrystallization from ether
  5. customgave (4.78 g; 65.4%)
  6. custom170-172° C.

Sources & evidence

ORD record
ord-14f1e1cffcb449c09da97e767783b332
Source dataset
uspto-grants-2013_10
Patent number
US08546309B2

Reaction notes

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