Diisopropylethylamine → HCID 86651587, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottomed flask containing 2,4-dichloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-5-amine (0.336 g, 1.354 mmol) in 2.0 mL of DMSO was added morpholine-3-carboxylic acid hydrochloride (0.295 g, 1.761 mmol) and DIPEA (1.183 ml, 6.77 mmol). The reaction mixture was stirred at 100° C. for 16 h. The reaction was cooled to room temperature, diluted with 30 mL of water, transferred to an appropriate separatory funnel and extracted with EtOAc (3×25 mL). The organic layers were combined, washed with sat. NaCl, dried over Na2SO4, filtered and concentrated in vacuo affording an oil. The oil was suspended in 10 mL of Et2O, added 2 drops of EtOH and sonicated until a yellow precipitate appeared. Let mixture sit at room temperature for 1 h, collected solids by vacuum filtration, washed with additional Et2O, hexanes and dried under high vacuum affording 2-chloro-5-(tetrahydro-2H-pyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one. (90 mg, 20.4% yield) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.54-1.65 (m, 1H) 1.70 (dd, J=12.88, 2.02 Hz, 1H) 2.51-2.70 (m, 2H) 3.03 (ddd, J=13.58, 12.32, 3.92 Hz, 1H) 3.41-3.66 (m, 4H) 4.03 (dd, J=11.87, 3.79 Hz, 4H) 4.32-4.47 (m, 2H) 4.59 (tt, J=12.47, 4.07 Hz, 1H) 8.05 (s, 1H). MS [M+H] found 325.2.

Provenance & Evidence