Pyrrolo[2,1-f][1,2,4]triazin-4-aMine, 2-Methyl- synthesis

Yield:937047-44-4 57%

Reaction Conditions:

with potassium phosphate in butan-1-ol; for 166.5 h;Heating / reflux;

Steps:

AA

A mixture of 1-amino-1 H-pyrrole-2-carbonitrile hydrochloride (2.77 g, 19.3 mmol), potassium phosphate (21.11 g, 96.5 mmol), acetamidine hydrochloride (9.6 g, 96.5 mmol) and 1-butanol (166 mmol) was refluxed under nitrogen atmosphere. After 166.5 h of reflux, the mixture was allowed to cool to rt, and was then partitioned between ethyl acetate and water. The phases were separated, and the organic phase was extracted with 1 N aqueous hydrochloric acid. The acid extracts were made basic (pH > 7) and extracted with ethyl acetate. After washing the organic layers with water and brine, drying (anhydrous sodium sulfate) and concentration afforded 1.63 g (57%) of solid. ¹H-NMR (CD₂ Cl₂): δ 7.51 (m, 1 H), 6.40 (m, 2 H), 6.72 (br s, 2 H), 2.32 (s, 3 H). MS: LC/MS (+esi), m/z = 149 [M+H]. RT = 1.12 min.

References:

WO2007/56170,2007,A2 Location in patent:Page/Page column 104