Triethylamine → 6-Chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine

HRID 1246784Notes

Reaction equation

HRID 1246784 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][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3O)=[CH:4][CH:3]=1.C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:34]>C1(C)C=CC=CC=1>[Cl:34][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][CH:20]=[CH:19][C:18]=1[Cl:23])[N:8]2[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178517925HCID 178517925, compound

Product 1

HCID 219057796-Chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9-(4-Chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-ol I-(4A-7)b (2.49 g, 6.97 mmol) was suspended in 50 ml of toluene. Triethylamine (1.07 ml, 7.68 mmol) was added followed by addition of POCl3 (720 μl, 7.72 mmol) at room temperature. The reaction was warmed to reflux and stirred for 23 hours to give a clear orange solution. After cooling the reaction to room temperature it was concentrated under reduced pressure, diluted with isopropanol (50 ml) and then concentrated further under reduced pressure until copious amount of precipitate came out of solution. The concentrated suspension was cooled in an ice bath and stirred for 2 hours. The precipitate was collected on a sintered glass funnel and rinsed with cold isopropanol to afford, after drying in vacuo, I-(4A-7)c as an off-white solid (2.13 g, 82%): +ESI MS (M+1) 375.1; 1H NMR (400 MHz, DMSO-d6) δ 8.84 (s, 1H), 7.76 (dd, J=7.46, 1.2 Hz, 1H), 7.58–7.40 (m, 7H).

Workup

  1. temperatureThe reaction was warmed
  2. temperatureto reflux
  3. customto give a clear orange solution
  4. temperatureAfter cooling
  5. customthe reaction to room temperature it
  6. concentrationwas concentrated under reduced pressure
  7. additiondiluted with isopropanol (50 ml)
  8. concentrationconcentrated further under reduced pressure until copious amount of precipitate
  9. temperatureThe concentrated suspension was cooled in an ice bath
  10. stirringstirred for 2 hours
  11. customThe precipitate was collected on a sintered glass funnel
  12. washrinsed with cold isopropanol
  13. customto afford
  14. dry with materialafter drying in vacuo, I-(4A-7)c as an off-white solid (2.13 g, 82%)

Sources & evidence

ORD record
ord-8b5b4a2401b54809a1859f01937ebb92
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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