Phosphorus oxychloride → 2-Amino-6-chloropurine

HRID 648677Notes

Reaction equation

HRID 648677 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 42%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of guanine (4.5g, 30 mmol), tetraethylammonium chloride (7.46 g, 45 mmol monohydrate, pre-dried), phosphorus oxychloride (16.5 ml) and acetonitrile (60 ml) was heated under reflux for 70 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 (24 hours) with ethyl acetate afforded 2-amino-6-chloropurine as a white solid (2.12 g, 42%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 70 minutes
  3. temperatureto cool
  4. filtrationThe solid material was filtered off
  5. extractionContinuous extraction (24 hours) with ethyl acetate

Sources & evidence

ORD record
ord-7a948373683e4eee821843603e62337a
Source dataset
uspto-grants-1988_04
Patent number
US04736029

Reaction notes

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