Diisopropylethylamine → 4H-Pyrido[1,2-a]pyrimidin-4-one

Temperature

110 °C

A mixture of 6-bromopurine (0.02040 g, 0.1025 mmol), 2-(aminomethyl)-3-(3-fluorophenyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.02420 g, 0.08542 mmol), and DIEA (0.04464 mL, 0.2563 mmol) in 1-butanol (2.000 mL) was stirred at 110° C. After 18 h, the mixture was removed from the heat and concd under reduced pressure. The crude mixture was purified by revered-phase semi-prep HPLC using 20-70% gradient of CH3CN (0.1% of TFA) in water (0.1% of TFA) over 40 min as eluent. The acetonitrile was concd under reduced pressure and to the remaining acidic aq layer was added satd NaHCO3 to neutralize the TFA salt. The resulting precipitate was collected by filtration and washed with water to give 3-(3-fluorophenyl)-6-methyl-249H-purin-6-ylamino)methyl)-4H-pyrido[1,2-a]pyrimidin-4-one as a light yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.87 (1 H, s), 8.07-8.16 (2 H, m), 7.68 (1 H, dd, J=9.0, 7.0 Hz), 7.55 (1 H, s), 7.39-7.51 (2 H, m), 7.24-7.31 (2 H, m), 7.15-7.23 (1 H, m), 6.92-7.00 (1 H, m), 4.51 (2 H, br. s.), 2.92 (3 H, s); Mass Spectrum (ESI) m/e=402.1 (M+1).

1. customthe mixture was removed from the
2. temperatureheat
3. customThe crude mixture was purified by revered-phase semi-prep HPLC
4. customover 40 min
5. additionwas added satd NaHCO3
6. filtrationThe resulting precipitate was collected by filtration
7. washwashed with water

ORD record

ord-a462b6d650db4109a94b8beab57aa644

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754089B2