HCID 178452709, compound → HCID 178452708, compound
Reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[CH:20]=[C:19]([OH:21])[N:18]=[C:17](S)[N:16]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]2[CH:20]=[C:19]([OH:21])[N:18]=[CH:17][N:16]=2)=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 92.5 °C
Procedure
Raney Nickel (6.0 g, in EtOH) is added to a suspension of [4-(6-hydroxy-2-mercapto-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester (2.0 g, 5.99 mmol) in MeOH (58 mL), under an argon atmosphere. The resulting mixture is heated to reflux for 2 h (oil bath is pre-heated to 90-95° C.), allowed to cool to rt, filtered through a pad of celite and concentrated in vacuo. The residue is purified by silica gel (160 g) column chromatography (CH2Cl2/MeOH, 95/5, then 90/10) to provide the title compound as a white solid: ES-MS: 302.1 [M+H]+; single peak at tR=6.54 min (System 2); Rf=0.34 (CH2Cl2/MeOH, 90/10).