Methanol → HCID 178449424, compound

Temperature

80 °C

5-Amino-N4-(1,1-dimethylethyl)-N1-methyl-1H-imidazole-1,4-dicarboxamide 6 (10.4 g, 0.041 mol, 93% pure), MeOH (100 mL) and Et3N (5 mL) were placed into a 250 mL, three-necked flask equipped with a nitrogen inlet, a gas outlet tube, reflux condenser, thermometer, magnetic stirrer bar, and maintained under a positive pressure of nitrogen. The mixture was heated at 80° C. (oil bath) for 3 hour with vigorous stirring (when HPLC analysis indicated that no more starting material was present), gradually cooled to room temperature, and concentrated under reduced pressure. The gummy residue was treated with a solution of t-BuOMe (10 mL), n-heptane (100 mL) and acetone (2 mL), and stirred at room temperature for 1 hour. The resulting precipitate was collected by vacuum filtration and dried (20 mm Hg, 20° C., 18 hours) to yield 8.9 g (theoretical yield is 7.37 g) of 5-amino-N-(1,1-dimethyl-ethyl)-1H-imidazole-4-carboxamide 17 as a tan solid.

1. customequipped with a nitrogen inlet, a gas outlet tube
2. temperaturereflux condenser
3. temperaturethermometer, magnetic stirrer bar, and maintained under a positive pressure of nitrogen
4. temperaturegradually cooled to room temperature
5. concentrationconcentrated under reduced pressure
6. additionThe gummy residue was treated with a solution of t-BuOMe (10 mL), n-heptane (100 mL) and acetone (2 mL)
7. stirringstirred at room temperature for 1 hour
8. filtrationThe resulting precipitate was collected by vacuum filtration
9. customdried (20 mm Hg, 20° C., 18 hours)

ORD record

ord-8840fd09c3f74451a617f7dd635219fa

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07446209B2