Triethylamine → (2-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)(pyridin-3-yl)methanone

A solution of nicotinoyl chloride (0.230 g, 1.62 mmol) in anhydrous THF (1.5 mL) was treated with 2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (0.250 g, 1.47 mmol) and triethylamine (0.3 g, 3.0 mmol) and subsequently allowed to stir at room temperature. After 4 hours the reaction was quenched with deionized H2O (10 mL). Following dilution with EtOAc (10 mL) the reaction mixture was washed twice with brine and once with saturated Na2HCO3(aq). The combined aqueous layers were then washed once with EtOAc. The combined organic layers were dried over anhydrous Na2SO4(s), filtered and then concentrated in vacuo. Purification over silica using a Methanol/CHCl3 gradient afforded the desired product in 87.9% yield (0.356 g, 1.3 mmol).

1. customAfter 4 hours the reaction was quenched with deionized H2O (10 mL)
2. washwas washed twice with brine and once with saturated Na2HCO3(aq)
3. washThe combined aqueous layers were then washed once with EtOAc
4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4(s)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customPurification over silica using a Methanol/CHCl3

ORD record

ord-3015f49062104a2380440d20d6312900

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296747B1