Phosphorus oxychloride → 2-Amino-6-chloropurine

HRID 275000Notes

Reaction equation

HRID 275000 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 39%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

4.5 g (0.03 mol) of guanine (manufactured by Sumika Fine Chemicals Co., Ltd.), 7.5 g (0.045 mol) of tetraethylammonium chloride and 27.1 g (0.177 mol) of phosphorus oxychloride were added to 60 ml of acetonitrile, followed by stirring for 70 minutes under heating refluxing conditions. After cooling, the crystal was collected by filtration and suspended in 50 ml of water. This suspension was made alkaline with a 30% aqueous solution of sodium hydroxide and then adjusted to a pH of 7 with 1N hydrochloric acid. The resulting crystal was collected by filtration and dissolved in 50 ml of 25% aqueous ammonia with heating, and the insoluble substances were filtered out. The mother liquor was concentrated under reduced pressure to yield 2.0 g (0.012 mol) of a precipitating crystal of 2-amino-6-chloropurine (yield 39%).

Workup

  1. temperatureunder heating
  2. temperaturerefluxing conditions
  3. temperatureAfter cooling
  4. filtrationthe crystal was collected by filtration
  5. filtrationThe resulting crystal was collected by filtration
  6. dissolutiondissolved in 50 ml of 25% aqueous ammonia
  7. temperaturewith heating
  8. filtrationthe insoluble substances were filtered out
  9. concentrationThe mother liquor was concentrated under reduced pressure

Sources & evidence

ORD record
ord-049d7a5bb3fb4f2e866e8cf0479725c1
Source dataset
uspto-grants-1995_02
Patent number
US05391733

Reaction notes

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