2,2-Diphenylethylamine → (1-{(1S,4R)-4-[2-Chloro-6-(2,2-diphenylethylamino)-purin-9-yl]-cyclopent-2-enyl}-1H-pyrazol-4-yl)-methanol

HRID 655132Notes

Reaction equation

HRID 655132 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([N:16]3[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=[N:17]3)[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.[C:24]1([CH:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:31][NH2:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([N:16]3[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=[N:17]3)[CH:13]=[CH:12]2)=[C:4]([NH:32][CH2:31][CH:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:3]=1

Participants

5

Reactant 3

HCID 775752,2-DiphenylethylamineHCID 81531DiisopropylethylamineHCID 86637576{1-[(1S,4R)-4-(2,6-Dichloro-purin-9-yl)cyclopent-2-enyl]-1H-pyrazol-4-yl}-methanol

Product 1

HCID 86645704(1-{(1S,4R)-4-[2-Chloro-6-(2,2-diphenylethylamino)-purin-9-yl]-cyclopent-2-enyl}-1H-pyrazol-4-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising {1-[(1S,4R)-4-(2,6-dichloro purin-9-yl)-cyclopent-2-enyl]-1H-pyrazol-4-yl}-methanol (0.675 g, 1.92 mmol), diphenylethylamine (0.398 g, 2.02 mmol) and DIPEA (0.298 g, 2.31 mmol) in dry THF (20 mL) is stirred at 35 C for 3 days. The solvent is removed in vacuo and the resulting crude residue is partitioned between DCM and 0.1 M HCl. The organic portion is separated, washed with water, brine, dried (MgSO4) and concentrated in vacuo to afford the title product.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe resulting crude residue is partitioned between DCM and 0.1 M HCl
  3. customThe organic portion is separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0905fb1ade4b4b02a95975cfbb8e738e
Source dataset
uspto-grants-2011_12
Patent number
US08071565B2

Reaction notes

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