Phosphorus oxychloride → 6-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine

HRID 1246781Notes

Reaction equation

HRID 1246781 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3O)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:28]>>[Cl:28][C:13]1[N:12]=[CH:11][N:10]=[C:9]2[C:14]=1[N:15]=[C:16]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])[N:8]2[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517926HCID 178517926, compound

Product 1

HCID 219058016-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine

Procedure

9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-ol I-(1A-1)c (6.5 g, 17 mmol) was heated to reflux in POCl3 (3 ml) overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved into chloroform and poured onto ice. The organic layer was separated and washed with saturated aqueous NaHCO3; the organic layers were combined, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was taken up in 1:1 methylene chloride/diethyl ether (200 ml) and was then filtered to remove residual starting material. Concentration of the organic layer gave the title compound I-(1A-1)d as a yellow foam (5.8 g, 85%): +ESI MS (M+1) 411.4; 1H NMR: (400 MHz, DMSO-d6): δ 8.83 (s, 1H), 7.79–7.75 (m, 2H), 7.63–7.58 (m, 1H), 7.56 (d, J=8.7 Hz, 2H), 7.42 (d, J=6.7 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved into chloroform
  3. additionpoured onto ice
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. filtrationwas then filtered
  10. customto remove residual

Sources & evidence

ORD record
ord-2d119b6a7a03459da4bf53a940feefb1
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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