Potassium Carbonate → HCID 86662075, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]#[C:23][Si](C)(C)C)=[N:20][C:19]([N:28]2[CH2:33][CH2:32][N:31]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])[CH2:30][CH2:29]2)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[C:11]([O:10][C:9]([N:8]([C:16]1[C:21]([C:22]#[CH:23])=[N:20][C:19]([N:28]2[CH2:33][CH2:32][N:31]([S:34]([CH2:37][CH3:38])(=[O:35])=[O:36])[CH2:30][CH2:29]2)=[CH:18][N:17]=1)[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:15])([CH3:12])([CH3:13])[CH3:14]Participants
4
Procedure
Tert-butyl N-tert-butoxycarbonyl-5-(4-(ethylsulfonyl)piperazin-1-yl)-3-((trimethylsilyl)ethynyl)pyrazin-2-ylcarbamate (589 mg, 1.037 mmol) was dissolved in anhydrous MeOH (10 mL) and treated with K2CO3 (14.33 mg, 0.1037 mmol). The reaction was allowed to stir at ambient temperature for 45 minutes. The solvent was removed in vacuo and the residue redissolved in DCM and washed with water followed by brine. The solution was dried (MgSO4), filtered and concentrated and the residue was purified by column chromatography (ISCO Companion™, 24 g column, 0-100% EtOAc/Petrol) to afford the title compound as an orange solid (287 mg, 60% Yield). 1H NMR (400.0 MHz, DMSO) d 1.23 (t, J=7.4 Hz, 3H), 1.38 (s, 18H), 3.11 (q, 2H), 3.26-3.34 (m, 4H), 3.69-3.71 (m, 4H), 4.65 (s, 1H) and 8.27 (s, 1H) ppm; MS (ES+) 396.0