Acetic Acid Mixture with Hydrobromic Acid → HCID 178515741, compound
Reaction equation
[NH2:1][C:2]1[C:3](/[CH:9]=[CH:10]/[C:11]([O:13]CC)=O)=[N:4][C:5](I)=[N:6][CH:7]=1.[BrH:16].C(O)(=O)C>>[Br:16][C:5]1[N:6]=[CH:7][C:2]2[N:1]=[C:11]([OH:13])[CH:10]=[CH:9][C:3]=2[N:4]=1Participants
3
Procedure
A 3-necked roundbottom flask, was charged with (E)-ethyl 3-(5-amino-2-iodopyrimidin-4-yl)acrylate (120 g, 388 mmol) followed by hydrogen bromide/acetic acid (1500 ml). The resulting solution was allowed to react, with stirring, for 1.5 hours while the temperature was maintained at 40˜50° C. Upon completion, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in 500 ml of methanol and the pH was adjusted to 7 by the addition of sodium bicarbonate. The resulting mixture was washed once with a solution of 46 g of NaHSO3 in 200 mL of water. The organic layer was concentrated under reduced pressure. The resulting slurry was filtered and the solids collected to afford the title compound.