Formaldehyde → 1-[(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)methyl]pyrrolidin-3-ol
Reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[CH2:7]=O.[N:9]1[N:10]2[CH:18]=[CH:17][CH:16]=[C:11]2[C:12]([NH2:15])=[N:13][CH:14]=1>C(O)(=O)C>[NH2:15][C:12]1[C:11]2=[CH:16][CH:17]=[C:18]([CH2:7][N:1]3[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]3)[N:10]2[N:9]=[CH:14][N:13]=1Participants
5
Procedure
3-Pyrrolidinol (1.56 g, 17.9 mmol) and 37% formalin solution (1.45 g, 17.9 mmol) were dissolved in acetic acid (75 mL) and stirred at room temperature for 10 min. To this solution was added a solution of pyrrolo[2,1-f][1,2,4]triazin-4-amine (2.0 g, 14.9 mmol) in acetic acid (75 mL), and the mixture was stirred at 60° C. for 4 h. After evaporation, the residue was taken up in 200 mL of 1 N aqueous potassium carbonate solution and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC (method 4) to give 390 mg (11% of th.) of the title compound.