5,6-DibroMothieno[2,3-d]pyriMidin-4(3H)-one synthesis

Yield:-

Reaction Conditions:

with bromine;sodium acetate;acetic acid for 27 h;Reflux;

Steps:

Thieno[2,3-<;i]pyrimidin-4(3H)-one, sodium acetate (20.92 g, 255 mmol), and bromine (3.0 ml, 58.2 mmol) in glacial acetic acid (100 ml) was stirred for 24 h. A second portion of bromine (10 ml, 194 mmol) was added and the heterogeneous mixture heated to reflux for 3 h, then cooled to ambient temperature. The mixture was diluted with saturated aqueous sodium sulfite and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with 99: 1 :0.1, 49: 1 :0.1, 24: 1 :0.1, and 23:2:0.2 methylene chloride:methanol:concentrated ammonium hydroxide as the eluant to afford 1.96 g (29% yield over two steps) of 5,6-dibromothieno[2,3-<;i]pyrimidin-4(3H)-one as a yellow solid. Method [8] retention time 6.19 min by ΗPLC (M+ 309, 311, and 313).

References:

WO2010/91310,2010,A1 Location in patent:Page/Page column 104