Hydrochloric Acid → 5-Methyl[1,3]oxazolo[4,5-b]pyridine-2(3H)-thione

Temperature

70 °C

Ammonium formate (1.64 g, 26 mmol) was added to a suspension of Pd(OH)2 on carbon (˜20% Pd, 0.73 g, 1.0 mmol) and 2-nitro-3-hydroxy-6-methylpyridine (2.0 g, 13 mmol) in EtOH (20 mL). The reaction mixture was heated to 70° C. for 1 h at which point the reaction mixture was allowed to cool to rt and was filtered through Celite®. The filtrate was concentrated under reduced pressure, yielding a thick orangish oil. The material was dissolved in EtOH (25 mL) and potassium hydroxide (0.875 g, 15.6 mmol) and carbon disulfide (15 mL) were added. The reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was acidified with 1 N HCl, and the resulting solid was collected by filtration. The solid was washed with water (2×) and air dried followed by drying in a 35° C. vacuum oven. LC-MS: RT=5.58 min, [M+H]+=167.0.

1. temperatureto cool to rt
2. filtrationwas filtered through Celite®
3. concentrationThe filtrate was concentrated under reduced pressure
4. customyielding a thick orangish oil
5. temperatureThe reaction mixture was heated
6. temperatureto reflux overnight
7. temperatureUpon cooling to rt
8. filtrationthe resulting solid was collected by filtration
9. washThe solid was washed with water (2×) and air
10. customdried
11. customby drying in a 35° C. vacuum oven

ORD record

ord-64982537af614bce91986c2fc8093296

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822472B2