(R)-6-Benzyl-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine → (R)-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

HRID 657782Notes

Reaction equation

HRID 657782 reaction equation
C([N:8]1[CH2:30][CH2:29][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:16][C@@H:17]([C:19]3[CH:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=3)[CH3:18])[C:10]=2[CH2:9]1)C1C=CC=CC=1>[Pd].CO>[F:28][C:25]([F:26])([F:27])[C:22]1[N:21]=[CH:20][C:19]([C@H:17]([NH:16][C:15]2[C:10]3[CH2:9][NH:8][CH2:30][CH2:29][C:11]=3[N:12]=[CH:13][N:14]=2)[CH3:18])=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 59840708(R)-6-Benzyl-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

Product 1

HCID 59840692(R)-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amineYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-6-benzyl-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (3.55 g, 8.59 mmol), 10% palladium on charcoal (740 mg), and methanol (60 mL) were stirred under hydrogen (1 atm) for 15 h. The catalyst was filtered off through Celite and the filter cake was washed with MeOH (3×30 mL). The filtrate was concentrated to obtain an off-white foam (2.74 g, 98% yield).

Workup

  1. filtrationThe catalyst was filtered off through Celite
  2. washthe filter cake was washed with MeOH (3×30 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-76b044b0dd6b41dbbafce2f1e6f88750
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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