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Step 3: Compound 10c (8.9 g, 40 mmol) was added to 100 mL of POCl3 and heated to reflux for 5 hours. After distilling off part of POCl3, ice water was added to the reminder. The mixture was adjusted with aqueous ammonia at a temperature of below 10° C to pH=7-8, and then extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and the solvent was concentrated to obtain Compound 10d (1.7 g, Yield 16.7percent). MS [M + 1]+ 255.1.
16.7%
for 5 h; Inert atmosphere; Reflux
Compound lOc (8.9 g, 40 mmol) was added to 100 mE of P0C13 and heated to reflux for 5 hours. Afier distilling off part of P0C13, ice water was added to the remindet The mixture was adjusted with aqueous ammonia at a temperature of below 10° C. to pH=7-8, and then extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and the solvent was concentrated to obtain Compound lOd (1.7 g,Yield 16.7percent). MS [M+1] 255.1.
With N-ethyl-N,N-diisopropylamine; In ethanol; at 20.0℃;Inert atmosphere;
Step 4: Compound 10d (1.5 g, 5.9 mmol), 3-amino-5-methyl-pyrazole (578 mg, 5.9 mmol) and diisopropyl ethylamine (1.5 g, 12 mmol) were added to a solution of 20 mL of ethanol. The mixture was stirred at room temperature overnight. The solvent was concentrated, and the remainder was separated by silica gel column to obtain Compound 9b 10e (650 mg, Yield 35%). MS [M + 1]+ 316.1.
35%
With N-ethyl-N,N-diisopropylamine; In ethanol; at 20.0℃;Inert atmosphere;
Compound 10d (1.5 g, 5.9 mmol), 3-amino-S-me- thyl-pyrazole (578 mg, 5.9 mmol) and diisopropyl ethylamine (1.5 g, 12 mmol) were added to a solution of 20 mEethanol. The mixture was stirred at room temperature overnight. The solvent was concentrated, and the remainder was separated by silica gel colunm to obtain Compound lOe (650 mg,Yield 35%). MS [M+1] 316.1.
With trichlorophosphate; for 5.0h;Inert atmosphere; Reflux;
Step 3: Compound 10c (8.9 g, 40 mmol) was added to 100 mL of POCl3 and heated to reflux for 5 hours. After distilling off part of POCl3, ice water was added to the reminder. The mixture was adjusted with aqueous ammonia at a temperature of below 10 C to pH=7-8, and then extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and the solvent was concentrated to obtain Compound 10d (1.7 g, Yield 16.7%). MS [M + 1]+ 255.1.
16.7%
With trichlorophosphate; for 5.0h;Inert atmosphere; Reflux;
Compound lOc (8.9 g, 40 mmol) was added to 100 mE of P0C13 and heated to reflux for 5 hours. Afier distilling off part of P0C13, ice water was added to the remindet The mixture was adjusted with aqueous ammonia at a temperature of below 10 C. to pH=7-8, and then extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and the solvent was concentrated to obtain Compound lOd (1.7 g,Yield 16.7%). MS [M+1] 255.1.
With N-ethyl-N,N-diisopropylamine; In ethanol; at 150.0℃; for 0.833333h;Microwave irradiation;
General procedure: The 2,4-dichloropyrimidine derivative 1 was dissolved in EtOHand 1.1 equiv. of the aniline derivative 2 and 1.1 equiv. of DIPEAwere added. The reactionwas carried out for 50 min at 150 C undermicrowave conditions. The reaction mixture was diluted with ethylacetate and washed with water. The organic phase was evaporatedand the crude intermediatewas used for the following reaction stepwithout purification.
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