Trifluoroacetic acid → Trifluoroacetic acid

HRID 1192408Notes

Reaction equation

HRID 1192408 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:23]=[CH:22][C:21]([CH3:24])=[N:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>CO.O=[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]3[CH2:23][CH2:22][CH:21]([CH3:24])[NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67539780HCID 67539780, compound

Product 2

HCID 6422Trifluoroacetic acidYield 27%HCID 67539197HCID 67539197, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(7-Methyl-pyrido[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (1.2 g, 3.64 mmol), PtO2 (42 mg, 0.18 mmol) in MeOH (40 mL) and TFA (2 mL) was stirred under H2 (1 atm) at room temperature for 4 hours. The catalyst was filtered and the solvent was removed. The residue was subject to column chromatography, eluted by DCM/MeOH (20:1) to give 4-(7-Methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester as TFA salt (0.43 g, 27%). 1H NMR (CDCl3, 400 MHz) δ 9.75 (s, 1H), 7.97 (s, 1H), 3.60 (m, 10H), 2.60 (m, 2H), 2.00 (m, 1H), 1.48 (s, 9H), 1.35 (d, J=6.4 Hz, 3H). MS (APCI+) [M+H]+334.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was removed
  3. washeluted by DCM/MeOH (20:1)

Sources & evidence

ORD record
ord-62ad1bc0b75c4565b5ca38be812057bb
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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