6-((2,2-Diphenylethyl)amino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrile → 2-(aminomethyl)-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

HRID 1293021Notes

Reaction equation

HRID 1293021 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]#[N:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>N.C(O)C.[Pd]>[NH2:20][CH2:19][C:17]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)=[C:10]([NH:9][CH2:8][CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:18]=1

Participants

5

Reactant 1

HCID 101593916-((2,2-Diphenylethyl)amino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrile

Product 1

HCID 229486282-(aminomethyl)-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amineYield 89.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

6-[(2,2-Diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrile (19.7 g, 0.046 mol) (Preparation 23) was dissolved in a saturated solution of ammonia in ethanol (500 ml). 10% Palladium on carbon (2 g) was added and the suspension was stirred under an atmosphere of hydrogen (414 kPa, 60 psi) for 36 hours. The suspension was filtered through Arbocel (Trade Mark) and the solvent was removed under reduced pressure. This gave the title compound as a foam (17.7 g).

Workup

  1. filtrationThe suspension was filtered through Arbocel (Trade Mark)
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3157cc26dcb94f829781f4c38e58ae1f
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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