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

HRID 20099

Reaktionsgleichung

Reaktionsgleichung von HRID 20099
FC(F)(F)C(O)=O.C([O:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=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:21]=[CH:20][N:19]=[CH:18][C:17]=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

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acid2×HCID 682631,1'-CarbonyldiimidazoleHCID 22293255Ethyl 4-[(4-[(tert-butoxycarbonyl)amino]pyridin-3-yl methyl)amino]piperidine-1-carboxylate

Produkt 1

HCID 22293216Ethyl 4-(2-oxo-1,4-dihydropyrido[4,3-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylateAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (0.50 mL) was a add to a solution of the material from Step A (0.24 g, 0.63 mmol) in dichloromethane (5 mL). After stirring overnight, another 0.5 mL of trifluoroacetic acid was added. After an additional 2 h, the reaction was concentrated. This material was dissolved in acetonitrile (5 mL) and carbonyldiimidazole (0.31 g, 1.89 mmol) was added at room temperature. After 2 h, 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, 10 to 15% methanol in methylene chloride gradient elution), which gave the title compound (0.089 g). MS 305.3.

Aufarbeitung

  1. waitAfter an additional 2 h
  2. concentrationthe reaction was concentrated
  3. dissolutionThis material was dissolved in acetonitrile (5 mL)
  4. waitAfter 2 h
  5. customthe acetonitrile was evaporated in vacuo
  6. customthe residue partitioned between 1N NaOH and dichloromethane
  7. dry with materialthe organic phase dried over magnesium sulfate
  8. customThe crude product was purified by chromatography (silica gel, 10 to 15% methanol in methylene chloride gradient elution), which

Quellen und Nachweise

ORD-Eintrag
ord-cd57a58e0f7a4147bb054cd46db949ec
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745427B2

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