Benzyl Alcohol → 2-chloro-6-phenylmethyloxy-1H-purine

HRID 275343Notes

Reaction equation

HRID 275343 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].Cl>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 53244122,6-Dichloropurine

Product 1

HCID 116518242-chloro-6-phenylmethyloxy-1H-purine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2,6-dichloropurine (0.30 g, 1.6 mmol) is added to a mixture of benzyl alcohol (0.19 g, 1.8 mmol) and 60% sodium hydride (0.13 g, 3.3 mmol) in DMF (8 ml) at room temperature (RT). After 1 hr, the reaction is heated to 60° C. for 18 hr, cooled to RT and dilute HCl is added to adjust the pH to 5. The mixture is extracted with EtOAc/THF 1:1, and the organic layer is dried over sodium sulfate, filtered and concentrated to give a solid. This is recrystallized from EtOAc/hexane to give the title compound, mp. 195°-196° C.

Workup

  1. temperaturecooled to RT
  2. extractionThe mixture is extracted with EtOAc/THF 1:1
  3. dry with materialthe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid
  7. customThis is recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-232e74ae26df45d58d1fdf663bff1601
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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