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

HRID 1168283
Notes
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Reaction equation

HRID 1168283 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.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[NH3:9].[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 222AmmoniaHCID 101593916-((2,2-Diphenylethyl)amino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carbonitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 222AmmoniaHCID 229486282-(aminomethyl)-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amineYield 153.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-[(2,2-diphenylethyl)amino]-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carbonitrile (5.70 g, 13.18 mmol) (Preparation 5) in ethanol (200 ml) saturated with ammonia gas was treated with Pearlman's catalyst (1.00 g), pressurised to 414 kPa (60 psi) with hydrogen in a sealed vessel and stirred at room temperature for 30 hours. The suspension was filtered through a pad of Arbocel (trade mark) and the solvent was removed under reduced pressure. The residue was twice azeotroped from dichloromethane and then purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume) gradually changing to dichloromethane:methanol:0.88 ammonia (90:10:0.5 by volume) to afford the title compound (4.34 g).

Workup

  1. filtrationThe suspension was filtered through a pad of Arbocel (trade mark)
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was twice azeotroped from dichloromethane
  4. custompurified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume)

Sources & evidence

ORD record
ord-cf49ce7076a340d0a7eb2f898890c951
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06624158B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes