HCID 11255508, compound → HCID 67538462, compound

HRID 1192421Notes

Reaction equation

HRID 1192421 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][CH:21]=[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]>CO.C(O)(C(F)(F)F)=O.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][CH2:21][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]

Participants

5

Reactant 1

HCID 11255508HCID 11255508, compound

Product 1

HCID 67538462HCID 67538462, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-pyrido[2,3-d]pyrimidin-4-yl-piperazine-1-carboxylic acid tert-butyl ester (0.24 g, 0.76 mmol) in MeOH (10 mL) and TFA (1 mL) was added PtO2 (10 mg). The mixture was stirred under H2 (1 atm) at room temperature overnight. The catalyst was filtered off and the solvent was removed. The residue was subject to column chromatography, eluted by DCM/MeOH (20:1) to afford 4-(5,6,7,8-Tetrahydro-pyrido[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.15 g, 62%). 1H NMR (CDCl3, 400 MHz) δ 8.10 (s, 1H), 5.92 (s, 1H), 3.50 (m, 4H), 3.40 (m, 2H), 3.25 (m, 4H), 2.55 (m, 2H), 1.85 (m, 2H), 1.48 (s, 9H). MS (APCI+) [M+H]+320.

Workup

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

Sources & evidence

ORD record
ord-beebd4bcfa5a4d4b9b278bf45968a7e7
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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