N,N-Diethylaniline → HCID 86685301, compound

Temperature

50 °C

To a flask charged with 7-(4-bromophenyl)imidazo[1,2-c]pyrimidin-5(6H)-one (25.00 g, 86.173 mmol), phosphoryl trichloride (31.554 mL, 344.69 mmol), and N,N-diethylaniline (27.420 mL, 172.35 mmol) was added acetonitrile (200 mL) and the mixture was heated to 50° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue diluted with water and DCM. The aqueous was neutralized with potassium carbonate and the bi-phasic mixture passed through a pad of celite to remove the insoluble material. The layers were separated and the aqueous extracted with DCM. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude material was triturated with hexanes and the solids were collected by filtration to afford 7-(4-bromophenyl)-5-chloroimidazo[1,2-c]pyrimidine (10.369 g, 33.604 mmol, 38.997% yield). MS (apci) m/z=310.0 (M+H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionthe residue diluted with water and DCM
3. customto remove the insoluble material
4. customThe layers were separated
5. extractionthe aqueous extracted with DCM
6. dry with materialThe combined organic layers were dried over MgSO4
7. concentrationconcentrated under reduced pressure
8. customThe crude material was triturated with hexanes
9. filtrationthe solids were collected by filtration

ORD record

ord-f6b8bc0a647b480789c69f9d909b3143

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962596B2