Dimethylformamide → 1-(tert-Butylcarbamoyl)prop-1-en-2-yl 3-amino-6-chloropyrazine-2-carboxylate

Reaction equation

[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][N:7]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.[C:26]([N+:30]1O[C:32]([CH3:35])=[CH:33][CH:34]=1)([CH3:29])([CH3:28])[CH3:27].CN(C=[O:40])C>>[NH2:1][C:2]1[C:3]([C:9]([O:11][C:32]([CH3:35])=[CH:33][C:34](=[O:40])[NH:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][N:7]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 123191853-Amino-6-chloro-pyrazine-2-carboxylic acid

HCID 715549892-Tert-butyl-5-methyl-1,2-oxazol-2-ium hexafluoro-phosphate

Product 1

HCID 854380081-(tert-Butylcarbamoyl)prop-1-en-2-yl 3-amino-6-chloropyrazine-2-carboxylate

Procedure

To a mixture of 3-amino-6-chloropyrazine-2-carboxylic acid (1.00 g; 5.76 mmol) and triethylamine (2.40 ml; 17.3 mmol) in abs. DMF is added 2-tert-butyl-5-methyl-1,2-oxazol-2-ium hexafluoro-phosphate (4.93 g; 17.3 mmol). The mixture is stirred at r.t. over night. Ice-water is added. The supernatant is decanted from the resin-like product which is sufficiently pure to be further reacted