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

HRID 1354523Notes

Reaction equation

HRID 1354523 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 (33A, 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 (IN, 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 5 vacuo. The residue was recrystallized from ethanol (300 ml). Yield after drying, in vacuo, over an appropriate drying agent: 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 5 vacuo
  7. customThe residue was recrystallized from ethanol (300 ml)
  8. customYield
  9. customafter drying, in vacuo, over an appropriate drying agent

Sources & evidence

ORD record
ord-810d0199ce7343bdbb9adb711acfab97
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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