Hydrochloric Acid → HCID 53629168, compound

Temperature

60 °C

In a 250 ml, three-necked flask fitted with a magnetic stirrer, a reflux condenser and under inert atmosphere, 4-methoxy-1-methyl-1H-imidazole-5-carboxamide x93 (1.45 g, 9.5 mmol) is dissolved at room temperature in anhydrous THF (80 ml). Lithium aluminium hydride (685 mg, 18 mmol) is added by portions while the temperature is rising to 30° C. The mixture is stirred for 7 h at 60° C. and cooled down to room temperature. Then isopropanol is added and the mixture is stirred for a further 16 hours at room temperature. First HCl 37% (W/W) is added to the reactional mixture to reach pH 1, then 5 N KOH to adjust pH to 10. The solvents are removed under vacuum. The residue is dissolved in a mixture of CH2Cl2/MeOH (80/20), filtered through a celite pad and concentrated to dryness. Purification by preparative chromatography on silicagel (conditions: CH2Cl2/MeOH/NH4OH: 90/10/1 (v/v/v)) affords 500 mg of 1-(4-methoxy-1-methyl-1H-imidazol-5-yl)methanamine x94.

1. customis rising to 30° C
2. temperaturecooled down to room temperature
3. stirringthe mixture is stirred for a further 16 hours at room temperature
4. customThe solvents are removed under vacuum
5. dissolutionThe residue is dissolved in a mixture of CH2Cl2/MeOH (80/20)
6. filtrationfiltered through a celite pad
7. concentrationconcentrated to dryness
8. customPurification by preparative chromatography on silicagel (conditions: CH2Cl2/MeOH/NH4OH: 90/10/1 (v/v/v))

ORD record

ord-bf75b32a84074667a8deb170ba31cb1a

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586623B2