2,2-Diphenylethylamine → 2-Chloro-N-(2,2-diphenylethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 2268404Notes

Reaction equation

HRID 2268404 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4](Cl)[N:3]=1.C(N(C(C)C)C(C)C)C.[C:27]1([CH:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:34][NH2:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)(C)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH:35][CH2:34][CH:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:3]=1

Participants

5

Reactant 3

HCID 775752,2-DiphenylethylamineHCID 81531DiisopropylethylamineHCID 2702652,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Product 1

HCID 101813352-Chloro-N-(2,2-diphenylethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineYield 104.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of 2,6-dichloro-9-tetrahydro-2H-pyran-2-yl-9H-purine (preparation 5) (30.9 g, 0.11 mol) in isopropyl alcohol (600 ml) was treated with N-ethyl-N-isopropyl-2-propanamine (47.5 ml, 0.27 mol) and 2,2-diphenylethylamine (24.8 g, 0.13 mol) and the resulting mixture heated at reflux for 3 hr. The solvent was removed under reduced pressure, the residue dissolved in ethyl acetate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:hexane (40:60) gradually changing to ethyl acetate:hexane (60:40) to afford the title compound as a foam (49.7 g).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 3 hr
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in ethyl acetate
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:hexane (40:60)

Sources & evidence

ORD record
ord-6500455169ff49a2af8963edd3f1dbbf
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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