Ammonia → 2-Isopropoxy-2-(2-methylpyrimidin-5-yl)ethanamine

Reaction equation

[CH:1]([O:4][CH:5]([C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1)[C:6]#[N:7])([CH3:3])[CH3:2].N>CO.[Ni]>[CH:1]([O:4][CH:5]([C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1)[CH2:6][NH2:7])([CH3:3])[CH3:2]

Participants

Procedure

2-Isopropoxy-2-(2-methylpyrimidin-5-yl)acetonitrile (169 mg, 0.884 mmol) was dissolved in methanol (10 ml) and 7M NH3 in methanol (4 ml). Argon was bubbled through the solution for 5 minutes. To the reaction was added Raney nickel (100 mg, 1.704 mmol) and it was fitted with a H2-filled balloon. After stirring at room temperature for 20 hours LCMS shows only around 30% conversion and raney nickel (100 mg, 1.70 mmol) was added. The reaction was stirred for another 72 hours, then filtered through a plug of celite and concentrated in vacuo. The crude product used for next reaction without further purification.