Sodium Bicarbonate → HCID 178455829, Verbindung

HRID 44826

Reaktionsgleichung

Reaktionsgleichung von HRID 44826
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(O)=[O:28].[Na+]>C(O)=O>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([OH:28])[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 58405345HCID 58405345, Verbindung

Produkt 1

HCID 178455829HCID 178455829, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 16, 100 mg, 0.28 mmol) was dissolved in 3 mL of HCOOH. This mixture was heated to reflux for 18 h, then aqueous NaHCO3 was added and the mixture was extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure and chromatographed on flash silica gel (CH2Cl2:CH3OH=6:1) to give the title compound as a white solid (80 mg, 80% yield). 1H NMR (CD3OD) δ: 8.09 (s, 1H), 8.52 (d, 1H) 7.46 (s, 1H), 7.27 (m, 1H), 4.42-4.38 (m, 2H), 3.41 (s, 3H), 2.0-1.7 (m, 10H) and 0.86 ppm (t, 3H); LCMS: 354.2 m/z (M+H)+; ret. Time: 1.36 min (Analytical Method E).

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 18 h
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe combined organic phase was dried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on flash silica gel (CH2Cl2:CH3OH=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-13ea11e38ec64b1da35e2909c0c974ef
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541418B2

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