Carbonic acid-guanidine (1:1) → Ethyl-3-(2-amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-benzoate

HRID 1051986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051986
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][C:13](=O)[C:12](=[CH:17]N(C)C)[CH2:11]2)[CH:5]=1.[C:22](=O)(O)O.[NH2:26][C:27]([NH2:29])=[NH:28].O.O.O.C([O-])(=O)C.[Na+]>CCO>[CH2:1]([O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][C:13]3[N:28]=[C:27]([NH2:29])[N:26]=[CH:17][C:12]=3[CH2:11]2)[CH:5]=1)[CH3:22]

Komponenten

5

Edukt 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 23665404Sodium Acetate TrihydrateHCID 86695813Methyl-3-(3-dimethylaminomethylene-4-oxopiperidin-1-yl)benzoate

Produkt 1

HCID 86695814Ethyl-3-(2-amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-benzoateAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of methyl-3-(3-dimethylaminomethylene-4-oxopiperidin-1-yl)-benzoate (1.52 g, 5.27 mmol) in EtOH (100 mL) was treated with guanidine carbonate (3.80 g, 21.08 mmol), followed by addition of sodium acetate trihydrate (5.74 g, 42.16 mmol). The reaction mixture was refluxed for 15 hours and the solvent was removed in vacuo. The residue was partitioned between water and ethyl acetate and the mixture was vigorously stirred at ambient temperature for several minutes. The yellow, amorphous precipitate was collected, washed with water, ethyl acetate, and dried to give 776 mg of the title compound. The ethyl acetate layer was dried (MgSO4), filtered, and concentrated.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 15 hours
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. customThe yellow, amorphous precipitate was collected
  5. washwashed with water, ethyl acetate
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dfeedbbfe2754e50949225cbd16e5046
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388176B2

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