Methyl 3-aminopyrazinecarboxylate → (3-Aminopyrazin-2-yl)methanol

Temperature

9 °C

Methyl-3-aminopyrazine-2-carboxylate (14.22 g, 93 mmol) was suspended in tetrahydrofuran (1 L) and cooled under a nitrogen atmosphere in a methanol/ice bath. Lithium aluminium hydride (100 ml, 1 M solution in diethyl ether, 100 mmol) was added at such a rate to maintain the temperature between 8-10° C. Once addition was complete the reaction was stirred at room temperature for 3 hours and then heated at reflux for 20 minutes. The reaction was then cooled to 0° C. and quenched with water (30 mL in 100 mL tetrahydrofuran) keeping the temperature below 8° C. The reaction was then stirred at room temperature for 30 minutes and then filtered. The residue was washed with hot ethyl acetate (250 mL×2) filtered. The two filtrates were combined and evaporated to dryness. This produced (3-amino-pyrazin-2-yl)methanol (7.38 g) as a pale orange solid.

1. temperaturecooled under a nitrogen atmosphere in a methanol/ice bath
2. additionOnce addition
3. temperatureheated
4. temperatureat reflux for 20 minutes
5. temperatureThe reaction was then cooled to 0° C.
6. customquenched with water (30 mL in 100 mL tetrahydrofuran)
7. customthe temperature below 8° C
8. stirringThe reaction was then stirred at room temperature for 30 minutes
9. filtrationfiltered
10. washThe residue was washed with hot ethyl acetate (250 mL×2)
11. filtrationfiltered
12. customevaporated to dryness

ORD record

ord-7a663f88a6b84b2db7dc549aaee3ca51

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07459454B2