Methylthiouracil → 4(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-

355 mg (2.5 mmol) of 6-methyl-2-thiouracil are dissolved in a sodium ethoxide solution prepared from 116 mg (5.05 mmol) of sodium metal and 15 ml of anhydrous ethanol. The mixture is gently warmed to dissolve the thiouracil, then 515 mg (2.5 mmol) of (2-chloromethylphenyl)-dimethylammonium chloride are added and the reaction mixture is refluxed under stirring for 1 hour. Sodium chloride is immediately precipitated from the solution. After evaporation under reduced pressure the residue is taken up in water, extracted 3 times with 20 ml of chloroform each, then the combined organic phase is washed with 20 ml of water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The pale yellow oily residue is rubbed with an 1:1 mixture of benzene and petroleum ether to obtain 287 mg (47.7%) of the title compound as a white crystalline product, m.p.: 151°-153° C.

1. temperatureThe mixture is gently warmed
2. temperaturethe reaction mixture is refluxed
3. customSodium chloride is immediately precipitated from the solution
4. customAfter evaporation under reduced pressure the residue
5. extractionextracted 3 times with 20 ml of chloroform each, then the combined organic phase
6. washis washed with 20 ml of water
7. dry with materialdried over anhydrous magnesium sulfate
8. customevaporated under reduced pressure
9. additionThe pale yellow oily residue is rubbed with an 1:1 mixture of benzene and petroleum ether

ORD record

ord-baa6d9552ea542a68ccfd12b5de6b346

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05037830