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

HRID 2219932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2219932
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

Komponenten

6

Edukt 2

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

Produkt 1

HCID 59021531N-(4-(Difluoromethoxy)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amineAusbeute 105,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cf65be0c55a2448aa0b6fc12c9bf002c
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07414131B2

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