6-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine → 6-tert-Butoxy-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine

HRID 1246809Notes

Reaction equation

HRID 1246809 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[CH3:26][C:27]([CH3:30])([O-:29])[CH3:28].[K+]>O1CCCC1>[C:27]([O:29][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[N:6]2[C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)([CH3:30])([CH3:28])[CH3:26]

Participants

4

Reactant 2

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

Product 1

HCID 103436036-tert-Butoxy-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d, potassium tert-butoxide (20 mg, 0.15 mmol) and tetrahydrofuran (1 ml) were combined and stirred overnight at ambient temperature. The reaction mixture was concentrated to dryness and the residue was extracted into ethyl acetate from saturated aqueous NaHCO3 solution. The organic layers were combined, dried (Na2SO4), filtered, and evaporated to dryness. The crude product was purified by chromatography on a preparative TLC plate using 4% methanol/methylene chloride as the solvent to give title compound 2A-1 as a yellow oil: +ESI MS (M+1) 447.5; 1H NMR (400 MHz, CD3OD) δ 8.48 (s, 1H), 7.64 (d, J=8.3 Hz, 1H), 7.55 (d, J=2.1 Hz, 1H), 7.49–7.44 (m, 3H), 7.34 (d, J=9.1 Hz, 2H), 1.77 (s, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionthe residue was extracted into ethyl acetate from saturated aqueous NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by chromatography on a preparative TLC plate

Sources & evidence

ORD record
ord-325195195e88408d8f253145396d57a4
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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