Trifluoroacetic acid → Ethyl 4-(2-oxo-1,4-dihydropyrido[3,4-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

HRID 271897

Reaction equation

HRID 271897 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([NH:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1)=O)(C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O>ClCCl>[O:12]=[C:13]1[NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[CH2:22][N:23]1[CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 22293284Ethyl 4-[({3-[(tert-butoxycarbonyl)amino]pyridin-4-yl}methyl)amino]piperidine-1-carboxylate

Product 1

HCID 22293189Ethyl 4-(2-oxo-1,4-dihydropyrido[3,4-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylateYield 39.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.43 g) was added to a solution of the material from Step A (0.47 g, 1.24 mmol) in dichloromethane (10 mL). After stirring overnight, the reaction was concentrated. This material was dissolved in acetonitrile (5 mL) and carbonyldiimidazole (0.62 g, 3.73 mmol) was added at room temperature. After 2 d, the acetonitrile was evaporated in vacuo, the residue partitioned between 1N NaOH and dichloromethane, and the organic phase dried over magnesium sulfate. The crude product was purified by chromatography (silica gel, 1 to 20% methanol in methylene chloride gradient elution), which gave the title compound (0.15 g). MS 305.2.

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutionThis material was dissolved in acetonitrile (5 mL)
  3. waitAfter 2 d
  4. customthe acetonitrile was evaporated in vacuo
  5. customthe residue partitioned between 1N NaOH and dichloromethane
  6. dry with materialthe organic phase dried over magnesium sulfate
  7. customThe crude product was purified by chromatography (silica gel, 1 to 20% methanol in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-c8e34e993521438780471d1edadd26b4
Source dataset
uspto-grants-2008_11
Patent number
US07452903B2

Linked notes

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