HCID 178418361, compound → HCID 178517782, compound

HRID 2406217Notes

Reaction equation

HRID 2406217 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([OH:18])=[N:13][C:12]([C:19]([F:22])([F:21])[F:20])=[N:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[F:22][C:19]([F:20])([F:21])[C:12]1[N:13]=[C:14]([OH:18])[C:15]2[CH2:16][CH2:17][NH:8][CH2:9][C:10]=2[N:11]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178517783HCID 178517783, compound

Product 1

HCID 178517782HCID 178517782, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 7-benzyl-2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-ol (0.47 g, 1.52 mmol) partially dissolved in methanol (20 mL) was added palladium hydroxide on carbon (70 mg, wet, 20% by weight dry basis). The reaction was stirred for 20 hours in a Parr shaker under a pressure of 50 psi hydrogen. The reaction was then filtered through a Celite plug, eluting with methanol (400 mL). The filtrate was concentrated in vacuo to yield 2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-ol as a light beige solid (255 mg, 77% yield). 1H NMR (400 MHz, MeOD) δ ppm 4.09 (s, 2H), 3.48 (t, J=6.32 Hz, 2H), 2.78 (t, J=6.32 Hz, 2H).

Workup

  1. filtrationThe reaction was then filtered through a Celite plug
  2. washeluting with methanol (400 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8756a7fa83404e0baeae97783c0bed27
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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