Ammonium formate → N-(4-(Difluoromethoxy)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971210Notes

Reaction equation

HRID 971210 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]([O:25][CH:26]([F:28])[F:27])=[CH:21][CH:20]=3)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.C(=O)(O)[O-].[Na+].[Pd]>[F:28][CH:26]([F:27])[O:25][C:22]1[CH:23]=[CH:24][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:20][CH:21]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 590215487-Benzyl-N-(4-(difluoromethoxy)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 59021531N-(4-(Difluoromethoxy)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amineYield 105.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

7-Benzyl-N-(4-(difluoromethoxy)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine (1.01 g, 2.65 mmol), ammonium formate (1.67 g, 26.46 mmol) and palladium, 10% wt. on activated carbon (100 mg) in methanol (20 mL) was heated to 60° C. for 1 h. The mixture was cooled to r.t. and filtered over celite. The filtrate was concentrated under reduced pressure to give a white solid which was taken up in saturated aqueous sodium bicarbonate. The mixture was extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to dryness to give 0.82 g of a tan solid. The compound was further purified by silica gel chromatography using a gradient of methanol:chloroform (0-20%) to give the desired compound as an white solid.

Workup

  1. filtrationfiltered over celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto give a white solid which
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5fe00fdcf8684402bf42106830fbcad8
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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