Triethylamine → (1S,2R,4R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-{6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}cyclopentanol

HRID 552735Notes

Reaction equation

HRID 552735 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][C@@H:13]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3Cl)[CH2:12][C@@H:11]1[OH:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[NH2:33][C@@H:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH2:35]1>C(O)C>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][C@@H:13]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3[NH:33][C@@H:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:36][CH2:35]2)[CH2:12][C@@H:11]1[OH:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70000841-Aminoindane, (S)-HCID 86607322(1S,2R,4R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(6-chloro-9H-purin-9-yl)cyclopentanol

Product 1

HCID 67164355(1S,2R,4R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-{6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}cyclopentanolYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (1S,2R,4R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(6-chloro-9H-purin-9-yl)cyclopentanol (0.091 g, 0.24 mmol), triethylamine (0.1 mL, 0.72 mmol) and (S)-1-aminoindane (0.0662 g, 0.48 mmol) in ethanol (5 mL) was refluxed at 95° C. for 14 h and then concentrated under reduced pressure. The residue was purified by flash chromatography (0 to 60% EtOAc/DCM) to afford the title compound (0.09 g, 80%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (0 to 60% EtOAc/DCM)

Sources & evidence

ORD record
ord-47ce8961693846dc841e13aec50ade7c
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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