2-ethylmorpholine

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6-bromo-3-iodo-N-(4-methoxybenzyl)quinolin-2-amine (0.30 g, 0.640 mmol, prepared as in Example 1, Step 1-2), 2-ethylmorpholine (1.105 g, 9.59 mmol), copper(I) iodide (6.09 mg, 0.032 mmol), cesium carbonate (0.417 g, 1.279 mmol), and 2-isobutyrylcyclohexanone (0.021 mL, 0.128 mmol) in DMF (3 mL) was heated at 125° C. for 10 min. Some product was observed but mostly starting material. The mixture was heated again at 125° C. for 10 min more. This process was repeated 3× until the starting material was completely consumed. The reaction was brought to RT, poured into water (20 mL) and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered, concentrated, and chromatographed on silica gel using gradient 2:1 hexanes/EtOAc to afford a brown oil as 6-bromo-3-(2-ethylmorpholino)-N-(4-methoxybenzyl)quinolin-2-amine. The mixture was heated again at 125° C. for 10 min more was completely consumed was brought to RT poured into water (20 mL) extracted with EtOAc The combined organics were dried over Na2SO4 filtered concentrated chromatographed on silica gel using gradient 2:1 hexanes/EtOAc

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-chlorophthalazin-1(2H)-one and 2-ethylmorpholine were processed using a method similar to that described in Example 1A to afford the title compound. MS (APCI+) M/Z 260 (M+H)+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-chlorophthalazin-1(2H)-one and 2-ethylmorpholine were processed using a method similar to that described in Example 1A to afford the title compound. MS (APCI+) M/Z 260 (M+H)+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-chlorophthalazin-1(2H)-one and 2-ethylmorpholine were processed using a method similar to that described in Example 1A to afford the title compound. MS (APCI+) M/Z 260 (M+H)+.

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a microwave tube, 0.45 g of 2-ethylmorpholine is placed in 10 ml of ethanol, 2.11 ml of N,N-diisopropylethylamine and 2.29 g of ethyl 3-ethoxy-3-iminopropanoate hydrochloride. The tube is then microwave-heated at 130° C. for 1 hour and then allowed to return to ambient temperature. The reaction mixture is concentrated under reduced pressure. After purification by silica column chromatography, eluent: 90/05 dichloromethane/methanol, 550 mg of [4-(2-ethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid ethyl ester are obtained in the form of a beige powder, the characteristics of which are the following: to return to ambient temperature The reaction mixture is concentrated under reduced pressure After purification by silica column chromatography, eluent

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6-bromo-3-iodo-N-(4-methoxybenzyl)quinolin-2-amine (0.30 g, 0.640 mmol, prepared as in Example 1, Step 1-2), 2-ethylmorpholine (1.105 g, 9.59 mmol), copper(I) iodide (6.09 mg, 0.032 mmol), cesium carbonate (0.417 g, 1.279 mmol), and 2-isobutyrylcyclohexanone (0.021 mL, 0.128 mmol) in DMF (3 mL) was heated at 125° C. for 10 min. Some product was observed but mostly starting material. The mixture was heated again at 125° C. for 10 min more. This process was repeated 3× until the starting material was completely consumed. The reaction was brought to RT, poured into water (20 mL) and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered, concentrated, and chromatographed on silica gel using gradient 2:1 hexanes/EtOAc to afford a brown oil as 6-bromo-3-(2-ethylmorpholino)-N-(4-methoxybenzyl)quinolin-2-amine. The mixture was heated again at 125° C. for 10 min more was completely consumed was brought to RT poured into water (20 mL) extracted with EtOAc The combined organics were dried over Na2SO4 filtered concentrated chromatographed on silica gel using gradient 2:1 hexanes/EtOAc