2-Chloropyrimidine-4-carbonitrile → HCID 21959645, compound

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[C:10](OC([O-])=O)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>CO.[Ni]>[C:13]([O:12][C:10](=[O:11])[NH:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

Procedure

2-Chloropyrimidine-4-carbonitrile (24 g), 40.8 g of t-butyl dicarbonate (Boc2O) in 1.2 L of methanol and 5 g of Raney nickel (Raney 2400) were charged in an autoclave. The autoclave was sealed and purged with hydrogen. The hydrogenation was run at 30 psi hydrogen gas. The reduction was carried out to completion and the reactor was vented and purged with nitrogen. The reaction mixture was filtered over diatomaceous earth and the filtrate was concentrated. The residue was purified by chromatography to yield the title compound (35 g, 84%) as white solid of melting point of 86-88° C.