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Ammonium formate → (S)-4-(methyl(piperidin-3-yl)amino)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one

HRID 919600
Notes
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Reaction equation

HRID 919600 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([N:14]([CH3:26])[C:15]2[C:16]3[CH2:24][CH2:23][C:22](=[O:25])[NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:26][N:14]([C@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)[C:15]1[C:16]2[CH2:24][CH2:23][C:22](=[O:25])[NH:21][C:17]=2[N:18]=[CH:19][N:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86706465(S)-4-((1-benzylpiperidin-3-yl)(methyl)amino)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 86706466(S)-4-(methyl(piperidin-3-yl)amino)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-oneYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887
Methanol
Solvent

Procedure

To a solution of (S)-4((1-benzylpiperidin-3-yl)(methyl)amino)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one (100 mg, 0.3 mmol) in MeOH (3 mL) was added 10% Pd/C (100 mg) and ammonium formate (179 mg, 2.8 mmol) and the reaction mixture was heated for overnight. The reaction mixture was filtered and concentrated in vacuo to afford (72 mg, 96%) of the titled intermediate which was used without purification. LC-MS: m/z [M+1]=262.

Workup

  1. temperaturethe reaction mixture was heated for overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed08e91d5bef4c609303c6a5de0aff94
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273028B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes