Dimethylbarbituric acid → N-(((2S,3R)-3-Methylpiperidin-2-yl)methyl)-5-(trifluoromethyl)pyridin-2-amine

HRID 60902

Reaktionsgleichung

Reaktionsgleichung von HRID 60902
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4](C(OCC=C)=O)[C@@H:3]1[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1.CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@@H:3]1[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][N:17]=1

Komponenten

5

Edukt 2

HCID 69860Dimethylbarbituric acidHCID 89748220(2S,3R)-Allyl 3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidine-1-carboxylate

Produkt 1

HCID 89739447N-(((2S,3R)-3-Methylpiperidin-2-yl)methyl)-5-(trifluoromethyl)pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (2S,3R)-allyl 3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidine-1-carboxylate (0.528 g, 1.48 mmol), Pd(PPh3)4 (0.086 g, 0.0074 mmol) and 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (0.14 g, 0.89 mmol) in DCM (20 mL) was stirred at rt. When the starting material was consumed as judged by reverse-phase HPLC analysis, the reaction was concentrated in vacuo. The crude residue was taken up in EtOAc, and washed with satd. aq. NaHCO3, brine, dried (MgSO4), and concentrated to obtain the crude which was purified by silica gel (0˜100% DCM/EtOAc) to afford the title compound. ESI-MS (m/z): 274 [M+1]+.

Aufarbeitung

  1. customWhen the starting material was consumed
  2. concentrationthe reaction was concentrated in vacuo
  3. washwashed with satd
  4. dry with materialaq. NaHCO3, brine, dried (MgSO4)
  5. concentrationconcentrated
  6. customto obtain the crude which
  7. customwas purified by silica gel (0˜100% DCM/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4075ba61013643928e15f440f765ce6f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440982B2

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