Pyridine → HCID 59239574, compound

Participants

Reaction Conditions

Reaction Steps

Step 3—Synthesis of 4-(7-(1-methyl-1H-imidazol-2-yl)-2-(4-nitrophenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)morpholine (mp): To a solution of product mo from step 2 (260 mg, 0.5 mmol) in pyridine (3 mL) was added dropwise 2,2-diethoxyethanamine (82 μL, 0.6 mmol) at rt. The resulting solution was heated at 115° C. for 3.5 hrs. After the reaction mixture cooled, it was concentrated in vacuo. The residue was treated with 2 N aqueous HCl (2.5 mL), and heated to reflux for 1 hr. The reaction solution was then cooled, and diluted with H2O, made basic with sat. aq. NaHCO3, extracted with EtOAc (3×10 mL). The combined organics were dried over Magnesium sulfate, filtered, concentrated onto Celite, and chromatographed (ISCO, 12 g column, 0-5% MeOH/EtOAc) to afford 113 mg (57%) of desired compound mp as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.59-8.53 (m, 2H), 8.32-8.26 (m, 2H), 6.83 (d, J=1.4, 1H), 6.74 (d, J=1.4, 1H), 4.38 (s, 2H), 3.91-3.85 (m, 4H), 3.62-3.56 (m, 7H), 3.38 (t, J=5.4, 2H), 2.90-2.84 (m, 2H). LC-MS: m/z=+422 (M+H)+.

Provenance & Evidence