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

HRID 2292237Notes

Reaction equation

HRID 2292237 reaction equation
[Na].[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([N-:15][CH:16]=[N:17]2)=[C:13]([N+](C)(C)C)[N:12]=1.Cl>CS(C)=O>[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([NH:15][CH:16]=[N:17]2)=[C:13]([O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:12]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5360545Sodium2×HCID 178483314HCID 178483314, compound

Product 1

HCID 116518242-chloro-6-phenylmethyloxy-1H-purineYield 79.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium spheres (250 mg, 10.87 mmol) and benzyl alcohol (2 ml, 19.33 mmol) were mixed and vigorously stirred under N2 at 60°-100° (oil-bath) until all the sodium had dissolved (30 minutes) The mixture was cooled to room temperature and a suspension of 2-chloro-6-trimethylammoniopurinide (100 g, .73 mmol) in sieve-dried DMSO (10 ml) was added. This was stirred at room temperature under N2 for 13/4 hours and the reaction mixture was then added dropwise to ice-H2O (100 ml). The pH of the solution was adjusted to 7.0 using lM HCl and the white solid which formed was filtered off, washing well on the pad with H2O. This material was dried in vacuo over P2O5 at room temperature to give 0 mg (79.5% yield) of product. An analytical sample was obtained by recrystallizing from ethanol-H2O and drying the product in vacuo. Analysis Calculated for:

Workup

  1. additionwere mixed
  2. dissolutionhad dissolved (30 minutes) The mixture
  3. additionwas added
  4. customthe white solid which formed
  5. filtrationwas filtered off
  6. washwashing well on the pad with H2O
  7. dry with materialThis material was dried in vacuo over P2O5 at room temperature

Sources & evidence

ORD record
ord-cbfb2c096fe74a7384892e9efa37ddf4
Source dataset
uspto-grants-1989_01
Patent number
US04801710

Reaction notes

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