Reaktion #1954225

Reaktionsgleichung

ethyl 5-{[3-chloro-4-[(2,4-difluorobenzyl)oxy]-6-methyl 2-oxopyridin-1(2H)-yl]methyl}pyrazine-2-carboxylate

NaBH4

→

desired compound

Ausbeute 44.0%

3-chloro-4-[(2,4-difluorobenzyl)oxy]-1-{[5-(hydroxymethyl)pyrazin-2-yl]methyl}-6-methylpyridin-2(1H)-one

Ausbeute 44.0%

Lösungsmittel

THF t-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with acetic acid (2 mL)
2. 2
   Sonstigethe solvent was removed in vacuo
3. 3
   SonstigeThe residue was triturated with water
4. 4
   Filtrationfiltered
5. 5
   WaschenThe solid was washed with fresh water
6. 6
   SonstigeThe solid was purified by flash column chromatography (100% ethyl acetate)
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

To a suspension of ethyl 5-{[3-chloro-4-[(2,4-difluorobenzyl)oxy]-6-methyl 2-oxopyridin-1(2H)-yl]methyl}pyrazine-2-carboxylate (4.0 g, 8.9 mmol) in THF:t-butanol (1:1) (10 mL) was added NaBH4 (0.46 g, 12.4 mmol). The reaction stirred at room temperature under argon overnight. The reaction mixture was quenched with acetic acid (2 mL) and the solvent was removed in vacuo. The residue was triturated with water and filtered. The solid was washed with fresh water followed by ethanol. The solid was purified by flash column chromatography (100% ethyl acetate). The appropriate fractions were combined and concentrated under reduced pressure to afford the desired compound (1.58 g, 44%) as a white solid. 1H NMR (CD3OD, 400 MHz) δ 8.59 (s, 1H), 8.56 (s, 1H), 7.52 (m, 1H), 7.01 (m, 2H), 6.55 (m, 1H), 5.45 (s, 2H), 5.29 (s, 2H), 4.71 (2H), 2.54 (s, 3H); ES-HRMS m/z 408.0940 (M+H calculated for C19H17N3O3ClF2 requires 408.0921).

Quelle