Benzyl Alcohol → Sodium

HRID 614936Notes

Reaction equation

HRID 614936 reaction equation
[Na:1].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][O:13][CH2:14][CH2:15][O:16]C(=O)C2C=CC=CC=2)=[C:5](Cl)[N:4]=1.O.[CH2:27]([OH:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[Na:1].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][O:13][CH2:14][CH2:15][OH:16])=[C:5]([O:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:4]=1

Participants

6

Reactant 4

HCID 244Benzyl Alcohol2×HCID 962WaterHCID 5360545SodiumHCID 137857472-Amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine

Product 2

HCID 5360545SodiumHCID 205176972-Amino-6-benzyloxy-9-(2-hydroxyethoxymethyl)purine

Conditions

Temperature
120 °C

Procedure

A solution of sodium benzylate in benzyl alcohol was prepared from sodium (2.58 g) and benzyl alcohol (28 ml). The solution was heated to 120° C. and 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (3.47 g) was added over a 10 minute period. The reaction mixture was heated overnight with stirring at 120°-130° C. and then poured into a mixture of ice and water. The resulting mixture was extracted thoroughly with chloroform. The aqueous phase was neutralized with acetic acid, giving a white precipitate which was recrystallized from methanol and then from water to give analytically pure 2-amino-6-benzyloxy-9-(2-hydroxyethoxymethyl)purine, m.p. 291°-292° C. (dec.) in 50% yield.

Workup

  1. temperatureThe reaction mixture was heated overnight
  2. extractionThe resulting mixture was extracted thoroughly with chloroform
  3. customgiving a white precipitate which
  4. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-73b16c481801404c8d94a952c46fc1fa
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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