Reaction #171752

Reaction equation

guanidine hydrochloride

2-(2-chlorophenyl)-1-(4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-3-(dimethylamino)prop-2-en-1-one

potassium carbonate

→

282

5-(2-chlorophenyl)-4-(4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)pyrimidin-2-amine

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe whole was sealed
2. 2
   Temperaturecooled to room temperature
3. 3
   Concentrationconcentrated
4. 4
   workup.ADDITIONThe residue was diluted with water
5. 5
   Extractionextracted with ethyl acetate
6. 6
   OtherThe combined organics were purified by reverse phase HPLC

Procedure

To a solution of crude 2-(2-chlorophenyl)-1-(4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-3-(dimethylamino)prop-2-en-1-one (ca. 0.22 mmol) in ethanol (2 mL) was added potassium carbonate (87 mg, 0.63 mmol) and then guanidine hydrochloride (40 mg, 0.42 mmol). The whole was sealed and heated at 90° C. for 8 h, cooled to room temperature and concentrated. The residue was diluted with water and extracted with ethyl acetate. The combined organics were purified by reverse phase HPLC to give 282. MS (ESI) 406.2

Source