反応 #5424

反応方程式

diethyl 2-methylpyrimidine-4,5-dicarboxylate

2-amino-2,3-dimethylbutyramide

→

2-methyl-4-(4-methyl-4-isopropylimidazolin-5-on-2-yl)-pyrimidine-5carboxylic acid

収率 51.5%

溶媒

toluene

反応条件

後処理

1. 1
   温度the reaction mixture is cooled
2. 2
   その他the solid which has precipitated
3. 3
   ろ過is filtered
4. 4
   洗浄washed several times with diethyl ether
5. 5
   workup.DISSOLUTIONsubsequently dissolved in water
6. 6
   抽出the mixture is extracted five times
7. 7
   乾燥The combined organic extracts are dried over sodium sulphate
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The residue can be purified by chromatography on silica gel

実験手順

To a mixture of 98.8 g (0.415 mole) of diethyl 2-methylpyrimidine-4,5-dicarboxylate (compare, for example, J. Heterocycl. Chem. 2, 202-204 [1965]) and 54.0 g (0.415 mole) of 2-amino-2,3-dimethylbutyramide in 700 ml of anhydrous toluene there are added in portions 102.2 g (0.913 mole) of potassium tert.-butylate, and the mixture is subsequently stirred for 16 hours at 80° C. For working-up, the reaction mixture is cooled, the solid which has precipitated is filtered, washed several times with diethyl ether and subsequently dissolved in water. The aqueous solution is brought to pH 5 using half-concentrated hydrochloric acid, and the mixture is extracted five times using 200 ml portions of dichloromethane. The combined organic extracts are dried over sodium sulphate and concentrated in vacuo. The residue can be purified by chromatography on silica gel. 59 g (51% of theory) of 2-methyl-4-(4-methyl-4-isopropylimidazolin-5-on-2-yl)-pyrimidine-5carboxylic acid of melting point 56°-57° C. are obtained.

出典