Pyrimidine → 4-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

반응식

ClC[N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[N:5]([CH3:14])[S:4]1(=[O:16])=[O:15].N1C=CC=NC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][CH:11]([CH3:13])[CH2:10][CH2:9][CH:6]1[N:5]([CH3:14])[S:4](=[O:16])(=[O:15])[NH:3][C:7]1=[O:8]

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실험 절차

A mixture of 2-chloromethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 3.72 mmol), 2,4-dioxo-4-H-pyrido 1,2-a!pyrimidine (Formula IV: X=H; Y= ##STR18## (0.72 g; 4.44 mmol), and potassium carbonate (0.67 g; 4.84 mmol) in 35 ml of DMF was stirred at room temperature for 24 hours. The mixture was poured into ice/water, extracted with ethyl acetate, and the organic layer was washed with water, brine, and dried. The solvent was concentrated in vacuo and the residue purified by silica gel flash chromatography (70% hexane/ethyl acetate, 5% methanol/ethyl acetate) to afford 0.29 g of 2-(4-oxo-4-H-pyrido 1,2-a!pyrimidin-2-yl-oxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =H; R2 =(CH2)2CH(CH3); R3 =CH3 ; ##STR19## Example 1J) as a solid, m.p. 106.5°-107.5° C., and 0.34 g of 2-(4-oxo-4-H-2-hydroxypyrido 1,2-a!pyrimidin-3-yl-methyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide as a solid, m.p. 165°-170° C.