[CH3:1][N:2]1[C:6]([CH:7]=O)=[N:5][C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:3]1.[C:14](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO.C(OCC)C>[C:7]([C:6]1[N:2]([CH3:1])[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]=1)#[CH:14]
To a stirred mixture of 1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (2.06 g, 11.4 mmol) and potassium carbonate (3.16 g, 22.9 mmol) at room temperature in methanol (75 ml) under an argon atmosphere was added drop wise a solution of dimethyl 1-diazo-2-oxopropylphosphonate (2.64 g, 2.1 ml, 13.7 mmol) in methanol (15 ml). Stirring at room temperature was then continued for 3 h. The mixture was diluted with diethyl ether and washed with 10% NaHCO3 solution. The aqueous phase was extracted with diethyl ether. The combined organic layers were washed with H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography using a CH2Cl2MeOH gradient as eluent, providing the title compound (725 mg, 36%) as off-white solid. MS: m/z=177.2 (M+H+)
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