Sodium ethoxide → tert-Butyl 2-phenyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 394520

Reaktionsgleichung

Reaktionsgleichung von HRID 394520
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10](=[CH:15]N(C)C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.Cl.[C:21]([NH2:29])(=[NH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[O-]CC.[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:28]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:29]=[CH:15][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 16219042Benzamidine HCl hydrateHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Produkt 1

HCID 53946157tert-Butyl 2-phenyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-dimethylaminomethylene-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (prepared according to the method of Example 101, Step B, 509 mg, 2.0 mmol), benzamidine hydrochloride hydrate (470 mg, 3.0 mmol), and sodium ethoxide (1 M in ethanol, 6.0 mL, 6.0 mmol) in absolute ethanol (4 mL) was heated to reflux for about 3 d, cooled to room temperature, and concentrated. The residue was diluted with saturated aqueous sodium bicarbonate and extracted with chloroform (3×). The combined organic extracts were dried over sodium sulfate, filtered, evaporated, and purified by flash column chromatography (Biotage Flash 40S™, 10→15% ethyl acetate/hexanes) to give 304 mg (49%) of the title compound of Example 101, Step C as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 8.52 (s, 1H), 8.40-8.38 (c, 2H), 7.50-7.44 (c, 3H), 4.62 (s, 2H), 3.78 (t, 2H) 3.02 (t, 2H), 1.50 (s, 9H); MS (APCI) 312 (MH+).

Aufarbeitung

  1. customprepared
  2. temperaturewas heated
  3. temperatureto reflux for about 3 d
  4. concentrationconcentrated
  5. additionThe residue was diluted with saturated aqueous sodium bicarbonate
  6. extractionextracted with chloroform (3×)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. custompurified by flash column chromatography (Biotage Flash 40S™, 10→15% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-405f50dd49f74caa8676820a38f85338
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602875B2

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