Methanol → 4-benzyl-7-(hydroxymethyl)-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

温度

-78 °C

Methyl 4-benzyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate (600 mg, 2.02 mmol) was taken up in tetrahydrofuran (25 mL) in an inert environment. To the stirred suspension at room temperature was added NaH (60% dispersion in mineral oil, 121 mg, 3.03 mmo) and stirred 30 min. The reaction was then cooled to −78° C. and lithium aluminum hydride (3 mL, 2M in THF) was added. The reaction was stirred at a temperature between −20 and −10° C. for 2 h. The reaction was then cooled back to −78° C. and MeOH (1 mL) followed by water (1 mL) was added. The reaction was allowed to stir at ambient temperature for 2 h and then poured into ethyl acetate (200 mL) and water (100 mL). The biphasic mixture was stirred vigorously and then filtered through a medium frit. The layers were separated and the aqueous phase was extracted with ethyl acetate (2×50 mL). The organic layers were combined, washed with brine (100 mL), dried with sodium sulfate and concentrated to afford the title compound (540 mg, 99%) as a white solid. [M+H] calc'd for C15H15N3O2, 270; found, 270.

1. stirringThe reaction was stirred at a temperature between −20 and −10° C. for 2 h
2. temperatureThe reaction was then cooled back to −78° C.
3. additionwas added
4. stirringto stir at ambient temperature for 2 h
5. stirringThe biphasic mixture was stirred vigorously
6. filtrationfiltered through a medium frit
7. customThe layers were separated
8. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
9. washwashed with brine (100 mL)
10. dry with materialdried with sodium sulfate
11. concentrationconcentrated

ORDレコード

ord-b1bdeea83fc1406f9e590e6293c1b940

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08822470B2