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

HRID 60902
Notes
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Reaction equation

HRID 60902 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-4075ba61013643928e15f440f765ce6f
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440982B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes