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

HRID 1281076Notes

Reaction equation

HRID 1281076 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 (23, 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 vacuo, 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 vacuo

Sources & evidence

ORD record
ord-d7dac33b4ff7421e96e50f2f8e4d2547
Source dataset
uspto-grants-2002_09
Patent number
US06451968B1

Reaction notes

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