Dimethylformamide → 6-chloro-2-(trifluoromethyl)-7H-purine

HRID 1392113Notes

Reaction equation

HRID 1392113 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[NH:4][C:5](=O)[C:6]2[NH:7][CH:8]=[N:9][C:10]=2[N:11]=1.O=S(Cl)[Cl:17].CN(C=O)C>C(Cl)(Cl)Cl>[Cl:17][C:5]1[N:4]=[C:3]([C:2]([F:14])([F:13])[F:1])[N:11]=[C:10]2[C:6]=1[NH:7][CH:8]=[N:9]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1357425972-(Trifluoromethyl)-1,7-dihydro-6H-purin-6-one

Product 1

HCID 60539116-chloro-2-(trifluoromethyl)-7H-purineYield 45.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 15 g (73 mmol) of 2-trifluoromethylhypoxanthine and 300 mL of CHCl3 was warmed to reflux and treated with a solution of 26.7 mL (366 mmol) SOCl2 and 28.3 mL (366 mmol) DMF. The reaction was maintained at reflux for 1.5 h, cooled to room temperature, and poured into 1.2 L of ice-water. The organic layer was separated and washed with 2×300 mL of H2O. The pH of the combined aqueous phases was adjusted to 7 with saturated NaHCO3 and extracted with 3×1.2 L of ether. The combined ether and chloroform extracts were dried (MgSO4) and concentrated to dryness to give 7.4 g of crude product. 1H NMR (DMSO-d6) δ 14.45 (bs, 1H), 8.95 (s, 1H). MS (ES+) 222.96 (100%, M+H).

Workup

  1. temperaturewas warmed
  2. temperatureto reflux
  3. temperatureThe reaction was maintained
  4. temperatureat reflux for 1.5 h
  5. customThe organic layer was separated
  6. washwashed with 2×300 mL of H2O
  7. extractionextracted with 3×1.2 L of ether
  8. dry with materialThe combined ether and chloroform extracts were dried (MgSO4)
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-17f94e97eb174750821be869341c446b
Source dataset
uspto-grants-2008_03
Patent number
US07342021B2

Reaction notes

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