Dimethyl Sulfate → 1,3,6-Trimethyl-2,4(1H,3H)-pyrimidinedione
反応式
CC1OC(C2NC3C(=CC=CC=3)N3[C:8]2=[C:9]2[N:31]([CH3:32])[C:29](=[O:30])[N:28]([CH3:33])[C:26](=[O:27])[C:10]2=C3C2C=CC=CC=2)=CC=1.CC1NC(=O)NC(=O)C=1.COS(OC)(=O)=O>>[CH3:32][N:31]1[C:9]([CH3:8])=[CH:10][C:26](=[O:27])[N:28]([CH3:33])[C:29]1=[O:30]参加物
4
実験手順
Synthesis of PPQ-102—Synthesis of PPQ-102 was achieved in six steps as illustrated in FIG. 2B. Commercially available 6-methyluracil 1 was methylated using dimethylsulfate to produce 1,3,6-trimethyluracil 2, which upon Friedel-Crafts acylation using zinc chloride as a catalyst yielded 5-benzoyl-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione 3 as a white powder. Bromination of 3 followed by reaction with N-(2-aminophenyl)acetamide generated amino-protected intermediate 5. The acetamido function of 5 was hydrolyzed and resultant intermediate 6 was cyclocondensed with 5-methylfurfural to yield yellowish-white racemic PPQ-102 7. Aromatic compound 8, which lacks a stereocenter, was prepared from 7 by oxidation with potassium permanganate.