Toluene → 3-(3-chloro-4-morpholinophenyl)-2-((3-ethynylphenoxy)methyl)-6-methyl-pyrimidin-4(3H)-one

Temperature

165 °C

A mixture of N-(3-chloro-4-morpholinophenyl)-3-oxobutanamide (0.80 g, 2.85 mmol), 2-(3-ethynylphenoxy)acetamide (1.0 g, 5.71 mmol) and titanium tetraisopropanolate (6.76 mL) in xylene (20 mL) was stirred at 165° C. for 24 h. The mixture was cooled to rt and 50 mL of toluene and 60 mL of saturated NH4Cl aqueous solution were added. The resulting mixture was stirred at rt overnight and filtered and the filtrate was extracted with DCM (150 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (0.60 g, 50%). The compound was characterized by the following spectroscopic data:

1. temperatureThe mixture was cooled to rt
2. stirringThe resulting mixture was stirred at rt overnight
3. filtrationfiltered
4. extractionthe filtrate was extracted with DCM (150 mL×3)
5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

ORD record

ord-f1ff9925b828427189b31f80a9d6b9ee

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434695B2