2,2,2-Trifluoroethanol → 9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-6-(2,2,2-trifluoroethoxy)-9H-purine

HRID 1246811Notes

Reaction equation

HRID 1246811 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:12])([F:11])[CH2:9][OH:10].Cl[C:14]1[N:22]=[CH:21][N:20]=[C:19]2[C:15]=1[N:16]=[C:17]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=1[Cl:37])[N:18]2[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1>>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([N:18]2[C:17]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[N:16][C:15]3[C:19]2=[N:20][CH:21]=[N:22][C:14]=3[O:10][CH2:9][C:8]([F:12])([F:11])[F:7])=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 219058016-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purineHCID 23665647Potassium tert-butoxide

Product 1

HCID 219058129-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-6-(2,2,2-trifluoroethoxy)-9H-purine

Procedure

Potassium tert-butoxide (1 M in THF; 0.73 ml, 0.73 mmol) and 2,2,2-trifluoroethanol (2 ml) were stirred at room temperature and to this mixture was added 6-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d (100 mg, 0.24 mmol). The reaction mixture was stirred at room temperature for 3 days then quenched with H2O and diluted with chloroform. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by preparative TLC using 20% ethyl acetate/hexanes as the eluant to give title compound 5A-1 (20 mg, 17%): +ACPI MS (M+1) 473.1; 1H NMR: (400 MHz, CD3OD): δ 8.58 (s, 1H), 7.64 (d, 1H), 7.57 (d, 1H), 7.50–7.41 (m, 3H), 7.36 (d, 2H), 5.23 (q, 2H).

Workup

  1. customthen quenched with H2O
  2. additiondiluted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-39c2205e590246b8b27bd8ea4754587b
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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