[CH:1]1([C:4]2[N:9]=[C:8]([CH3:10])[C:7]([C:11]([OH:13])=O)=[CH:6][N:5]=2)[CH2:3][CH2:2]1.CN[C:16]1[N:17]=[N:18][CH:19]=[CH:20][CH:21]=1.[N:22]1C=CC=C[CH:23]=1.ClCCl.CO>ClCCl>[N:17]1[CH:16]=[CH:21][C:20]([N:22]([CH3:23])[C:11]([C:7]2[C:8]([CH3:10])=[N:9][C:4]([CH:1]3[CH2:2][CH2:3]3)=[N:5][CH:6]=2)=[O:13])=[CH:19][N:18]=12-Cyclopropyl-4-methyl-pyrimidine-5-carboxylic acid (200 mg, 1.12 mmol) was dissolved in anhydrous dichloromethane (20 ml). 4-N,N-Dimethylaminopyridine (23 mg, 0.2 mmol) and N,N-diisopropyl carbodiimide (0.17 ml, 1.12 mmol) were sequentially added and the reaction mixture was stirred at room temperature for 2 hours. Ak methylaminopyridazine (147 mg, 1.35 mmol) was dissolved in anhydrous dichloromethane (5 ml) and together with pyridine (0.35 ml, 1.12 mmol) added to the reaction mixture. Stirring at room temperature was continued for 15 hours. The progress of the reaction was monitored by thin layer chromatography (dichloromethane/methanol 9:1). The reaction mixture was diluted with dichloromethane (50 ml), washed two times with distilled water (5 ml each). The organic phase was dried over sodium sulfate and the organic solvent was evaporated in vacuo. The crude product was purified by flash chromatography (dichloromethane/methanol, gradient: 100/0 to 90/10 (v/v), duration: 50 min). The title compound was isolated as a brownish oil (119 mg, yield: 39%, purity: 95%).
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