Phosphorus oxychloride → 2-Amino-6-chloropurine

HRID 1415970Notes

Reaction equation

HRID 1415970 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(#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 58.1%

Reagents, catalysts & solvents 2

HCID 82326Triethylmethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of guanine (22.7 g, 0.15 mol), methyltriethylammonium chloride (TEMAC) (45.5 g, 0.3 mol), phosphorus oxychloride (82.6 ml, 0.9 mol) and acetonitrile (67 ml) was heated at 60° C. with stirring for 6 hours and then cooled to 10° C. The solid material was filtered off and suspended in water (300 mls). The aqueous mixture was brought to alkaline pH with aqueous sodium hydroxide to achieve dissolution and powdered carbon (6.8 g) added. The mixture was stirred for 1 hour and then filtered to remove the carbon. Acetone (72 mls) was added and then the pH reduced to 7 with dilute hydrochloric acid. The product was filtered off, washed with acetone/water (50:50 mixture, 50 mls), water (50 mls), acetone/water (50:50 mixture, 50 mls) and acetone (50 mls) and then dried to give 2-amino-6-chloropurine as a cream coloured solid (14.77 g, 54 % yield).

Workup

  1. temperaturecooled to 10° C
  2. filtrationThe solid material was filtered off
  3. dissolutiondissolution and powdered carbon (6.8 g)
  4. additionadded
  5. stirringThe mixture was stirred for 1 hour
  6. filtrationfiltered
  7. customto remove the carbon
  8. additionAcetone (72 mls) was added
  9. filtrationThe product was filtered off
  10. washwashed with acetone/water (50:50 mixture, 50 mls), water (50 mls), acetone/water (50:50 mixture, 50 mls) and acetone (50 mls)
  11. customdried

Sources & evidence

ORD record
ord-50afca99ae8c4c08a6ba297b9af471b4
Source dataset
uspto-grants-1999_06
Patent number
US05910589

Reaction notes

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