Question

4-methyl uracil from acetoacetate ester?​

Answer 1

Answer:

1. Procedure

Eighty grams (1.33 moles) of finely powdered urea is stirred into a mixture of 160 g. (155 cc., 1.23 moles) of ethyl acetoacetate (Note 1), 25 cc. of absolute alcohol (Note 2), and ten drops of concentrated hydrochloric acid in a 5-in. crystallizing dish. The reagents are mixed well, and the dish is covered loosely with a watch glass and placed in a vacuum desiccator over concentrated sulfuric acid. The desiccator is evacuated continuously with a water pump until the mixture has gone to dryness (Note 3), which usually requires from five to seven days (Note 4). The crude β-uraminocrotonic ester when thoroughly dry weighs 200–205 g.

The dry, finely powdered, crude β-uraminocrotonic ester is stirred into a solution of 80 g. (2 moles) of sodium hydroxide in 1.2 l. of water at 95°. The clear solution is then cooled to 65° and carefully acidified, while stirring, by the slow addition of concentrated hydrochloric acid. The 6-methyluracil precipitates almost immediately, and after the mixture is cooled the product is collected on a filter, washed with cold water, alcohol, and ether, and air-dried. The substance is obtained as a colorless powder of a high degree of purity, and the yield is 110–120 g. (71–77 per cent of the theoretical amount). For further purification the pyrimidine may be crystallized from glacial acetic acid. 6-Methyluracil decomposes above 300°.

2. Notes