Phosphorus oxychloride → 2-Amino-6-chloropurine

HRID 648678Notes

Reaction equation

HRID 648678 reaction equation
[NH:1]1[C:10](=O)[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].P(Cl)(Cl)([Cl:14])=O>[Cl-].C([N+](CC)(CC)CC)C.C(#N)C>[NH2:3][C:2]1[N:4]=[C:5]2[C:9]([NH:8][CH:7]=[N:6]2)=[C:10]([Cl:14])[N:1]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135398634Guanine

Product 1

HCID 53603492-Amino-6-chloropurineYield 30%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of guanine (4.5 g, 30 mmol), tetraethylammonium chloride (30 mmol), phosphorus oxychloride (16.5 ml and acetonitrile (60 ml) was placed in a flask in an ultrasonic bath at 60° C. for 2 hours. The mixture was then heated under reflux for 90 minutes and allowed to cool. The solid material was filtered off and suspended in water. The aqueous mixture was brought to alkaline pH with aqueous sodium hydroxide and back to pH 7 with dilute hydrochloric acid. Continuous extraction with ethyl acetate afforded 2-amino-6-chloropurine as a white solid (1.55 g, 30%).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 90 minutes
  3. temperatureto cool
  4. filtrationThe solid material was filtered off
  5. extractionContinuous extraction with ethyl acetate

Sources & evidence

ORD record
ord-cdb3ce80b365479c9589d80b1d6ecf11
Source dataset
uspto-grants-1988_04
Patent number
US04736029

Reaction notes

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