4-Methylmorpholine → HCID 178498437, compound

To a sample of 150 mg (0.47 mmol) of 5-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]thien-2-ylcarboxylic acid in a three-necked round bottomed flask under an atmosphere of nitrogen were added 3.6 mL anhydrous dimethylformamide and 0.11 mL (0.99 mmol) of N-methylmorpholine. The reaction mixture was stirred and 90 mg (0.51 mmol) of 2-chloro-4,6-dimethoxy-1,3,5-triazine were added at once. The reaction mixture was stirred at room temperature for 0.5 hours and 162 mg (1.25 mmol) of 3-carbomethoxypyrrolidine were added in 1.0 mL of dimethylformamide. After stirring at room temperature for another 3.5 hours, the reaction was concentrated in vacuo and the residue was chromatographed on silica gel with 2-8% CH3OH/CHCl3 to give 78 mg (40%) of methyl 1-{5-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]thien-2-ylcarbonyl}pyrrolidine-3-carboxylate as a white solid. Mass Spectrum (FAB+): M+1=432; IR (KBr, cm-1): 643, 734, 768, 809, 1219, 1336, 1417, 1464, 1601, 1684, 1736, 2854, 2924, 3390; UV (C2H5 OH): λmax =222 (ε=21034), 279 (ε=19777).

1. stirringThe reaction mixture was stirred at room temperature for 0.5 hours
2. stirringAfter stirring at room temperature for another 3.5 hours
3. concentrationthe reaction was concentrated in vacuo
4. customthe residue was chromatographed on silica gel with 2-8% CH3OH/CHCl3

ORD record

ord-b962160eaf154a6eb5da8cf777296700

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05786358