Sodium Hydroxide → (5-Chloropyrazin-2-yl)methanol

Temperature

-70 °C

Diisobutylaluminum hydride (4.29 mL, 4.29 mmol) was added dropwise over 5 min to a solution of methyl 5-chloropyrazine-2-carboxylate (185 mg, 1.07 mmol) in tetrahydrofuran (10 mL) at −70° C. under an atmosphere of nitrogen. The reaction mixture was stirred at −70° C. for 5 min and then allowed to reach ambient temperature and stirred over night. The reaction mixture was cooled on ice and approximately 2 mL of 1 M sodium hydroxide was added dropwise while stirring. The reaction mixture was diluted with diethyl ether and stirred for 45 min at ambient temperature and then filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography using a gradient of ethyl acetate in heptane to yield 43 mg (28%) of the title product; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.72 (d, 1 H), 8.52-8.55 (m, 1 H), 5.71 (t, 1 H), 4.64 (d, 2 H);

1. customto reach ambient temperature
2. stirringstirred over night
3. additionwas added dropwise
4. stirringwhile stirring
5. stirringstirred for 45 min at ambient temperature
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. customthe residue was purified by column chromatography

ORD record

ord-f3f7e780e6d24281be0bb5f72a82c395

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143408B2