1-(Diphenylmethyl)azetidin-3-ol → 6-(1-Benzhydrylazetidin-3-yloxy)-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine

HRID 1246810Notes

Reaction equation

HRID 1246810 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.[CH:26]([N:39]1[CH2:42][CH:41]([OH:43])[CH2:40]1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC(C)([O-])C.[K+]>O1CCCC1>[CH:26]([N:39]1[CH2:42][CH:41]([O:43][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[C:5]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[N:6]3[C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH2:40]1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 219058016-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purineHCID 23665647Potassium tert-butoxide

Product 1

HCID 219058196-(1-Benzhydrylazetidin-3-yloxy)-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (1 ml) solution of 6-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d (30 mg, 0.073 mmol) and 1-benzhydrylazetidin-3-ol (53 mg, 0.22 mmol) was added potassium tertbutoxide (24 mg, 0.22 mmol). The combined reagents were stirred overnight at ambient temperature. The reaction mixture was concentrated to dryness and the residue was extracted into ethyl acetate from saturated 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 3A-1 as a yellow oil. A solution of the material in methylene chloride was treated with excess 1 N HCl in diethyl ether, stirred, evaporated to dryness, and then triturated in diethyl ether to afford the hydrochloride salt of compound 3A-1 (14 mg, 31%): +ESI MS (M+1) 612.2; 1H NMR (400 MHz, CD3OD) δ 8.51 (s, 1H), 7.65–7.30 (m, 17H), 5.85–5.77 (br m, 2H), 4.75–4.60 (br m, 2H), 4.55–4.30 (br m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionthe residue was extracted into ethyl acetate from saturated 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-dbd3796273d2438a8476a05578e781c2
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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