Sodium Acetate → HCID 58431332, Verbindung
Reaktionsgleichung
Br[CH2:2][C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1.[C:18]([O-:21])(=[O:20])[CH3:19].[Na+]>C(#N)C>[C:18]([O:21][CH2:2][C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1)(=[O:20])[CH3:19]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate (1.62 g, 5.17 mmol, from Step A) was dissolved in acetonitrile (15 mL) and sodium acetate (2.8 g, 34 mmol) was added. The mixture was heated to 80° C. for 4 hours, then allowed to stand at room temperature overnight. Acetonitrile was removed in vacuo. The residue was partitioned between water and ethyl acetate and the aqueous layer was extracted with two further portions of ethyl acetate. The combined extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-60% EtOAc/hexanes afforded purified product (0.95 g, 63%). H NMR (300 MHz, CDCl3): δ 8.15 (s, 1H), 5.36 (s, 2H), 4.53 (q, 2H), 2.25 (s, 3H), 1.46 (t, 3H); LCMS (M+H)+: 293.0.
Aufarbeitung
- customAcetonitrile was removed in vacuo
- customThe residue was partitioned between water and ethyl acetate
- extractionthe aqueous layer was extracted with two further portions of ethyl acetate
- washThe combined extracts were washed with water
- dry with materialbrine, dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- washFlash chromatography, eluting with a gradient from 0-60% EtOAc/hexanes
- customafforded
- custompurified product (0.95 g, 63%)
Quellen und Nachweise
- ORD-Eintrag
- ord-9c25af91cb494a7fb65342f8a31ef36e
- Quelldatensatz
- uspto-grants-2015_01
- Patentnummer
- US08933085B2
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