(7-Benzyl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-(4-trifluoromethyl-phenyl)-amine → (5,6,7,8-Tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-(4-trifluoromethylphenyl)amine

HRID 971188Notes

Reaction equation

HRID 971188 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[F:28][C:25]([F:26])([F:27])[C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:14]2[C:15]3[CH2:16][CH2:17][NH:8][CH2:9][C:10]=3[N:11]=[CH:12][N:13]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 11246086(7-Benzyl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-(4-trifluoromethyl-phenyl)-amine

Product 1

HCID 59021462(5,6,7,8-Tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-(4-trifluoromethylphenyl)amineYield 91%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

7-Benzyl-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine (13 g, 33.8 mmol) was dissolved in methanol (50 mL) and palladium hydroxide (20% wt. % (dry basis) on carbon) was added (5.0 g). The mixture was shaken on a Parr Shaker under H2(g) atmosphere (60 PSI) for 20 hours. The mixture was filtered through celite and evaporated to give 9.0 g of material as a grey solid (91%). 1.5 g of this material was purified on alumina in 10% MeOH-DCM to give 600 mg of the pure compound as an off white solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-85a8203da49a4cfa8fca16d1aef391f8
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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