N-(2-Aminoethyl)piperidine → 6-[(2,2-Diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carboxamide

HRID 1168286Notes

Reaction equation

HRID 1168286 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19](OC)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:35][CH2:36][CH2:37][N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 10139253HCID 10139253, compound

Product 1

HCID 102809386-[(2,2-Diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carboxamideYield 85.4%

Procedure

Methyl 6-[(2,2-diphenylethyl)amino]-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carboxylate (Preparation 9) (100 mg, 0.22 mmol) and 1-(2-aminoethyl)piperidine (0.31 ml, 2.19 mmol) were heated together at 130° C. for 2 hours. The excess amine was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume) to afford the title compound as a yellow foam (104 mg).

Workup

  1. customThe excess amine was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume)

Sources & evidence

ORD record
ord-07a47b0a0a304553934b7022089eecbc
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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