Benzyl Alcohol → 2-Amino-6-Benzyloxy-9-Carboxymethylpurine

HRID 51176

Reaction equation

HRID 51176 reaction equation
[Na].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][C:13]([OH:15])=[O:14])=[C:5](Cl)[N:4]=1.[OH-].[Na+].[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][C:13]([OH:15])=[O:14])=[C:5]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:4]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 14798Sodium HydroxideHCID 41928332-Amino-6-chloro-9H-purine-9-acetic acidHCID 5360545Sodium

Product 1

HCID 100633112-Amino-6-Benzyloxy-9-Carboxymethylpurine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Sodium (2.0 g; 87.0 mmol) was dissolved in benzyl alcohol (20 ml) and heated to 130° C. for 2 h. After cooling to 0° C., a solution of 2-amino-6-chloro-9-carboxymethylpurine (4.05 g; 18.0 mmol) in DMF (85 ml) was slowly added, and the resulting suspension stirred overnight at 20° C. Sodium hydroxide solution (1N, 100 ml) was added and the clear solution was washed with ethyl acetate (3×100 ml). The water phase then was acidified to a pH of 3 with 4 N hydrochloric acid. The precipitate was taken up in ethyl acetate (200 ml), and the water phase was extracted with ethyl acetate (2×100 ml). The combined organic phases were washed with saturated sodium chloride solution (2×75 ml), dried with anhydrous sodium sulfate, and taken to dryness by evaporation, in vacuo. The residue was recrystallized from ethanol (300 ml). Yield after drying, in vacou, over sicapent: 2.76 g (52%). M.p. 159-65° C. Anal. (calc., found) C,(56.18; 55.97); H,(4.38; 4.32); N,(23.4; 23.10). 1H-NMR (DMSO-d6): 4.82 ppm. (s,2H); 5.51 (s,2H); 6.45 (s,2H); 7.45 (m,5H); 7.82 (s,1H).

Workup

  1. temperatureAfter cooling to 0° C.
  2. washthe clear solution was washed with ethyl acetate (3×100 ml)
  3. extractionthe water phase was extracted with ethyl acetate (2×100 ml)
  4. washThe combined organic phases were washed with saturated sodium chloride solution (2×75 ml)
  5. dry with materialdried with anhydrous sodium sulfate
  6. customtaken to dryness by evaporation, in vacuo
  7. customThe residue was recrystallized from ethanol (300 ml)
  8. customYield
  9. customafter drying, in vacou

Sources & evidence

ORD record
ord-4dd5666674754d35be05eca274aae6e7
Source dataset
uspto-grants-2004_03
Patent number
US06713602B1

Linked notes

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