Triethylamine → 2-Chloro-4-sec. butylamino-5-nitro-6-methylpyrimidine

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[N:14]=[C:13](Cl)[C:12]([N+:16]([O-:18])=[O:17])=[C:11]([CH3:19])[N:10]=1.[CH:20]([NH2:24])([CH2:22][CH3:23])[CH3:21]>C(O)C>[Cl:8][C:9]1[N:14]=[C:13]([NH:24][CH:20]([CH2:22][CH3:23])[CH3:21])[C:12]([N+:16]([O-:18])=[O:17])=[C:11]([CH3:19])[N:10]=1

Participants

Procedure

15 ml of triethylamine are added to a solution of 15.6 g of 2,4-dichloro-5-nitro-6-methylpyrimidine (0.075 mole) in 300 ml of absolute ethanol. With ice cooling, 6.6 g of sec. butylamine (0.09 mole) are added dropwise at 0°-5° C over the course of c. 40 minutes to the dark red solution. After the mixture has been stirred for c. 3/4 hour at this temperature, it is poured into c. 700 ml of ice water and the water is extracted 3 times with ether. The ethereal extracts are dried over magnesium sulphate and evaporated. The resultant red oily substance is crystallised from petroleum ether to yield 10.5 g of 2-chloro-4-sec. butylamino-5-nitro-6-methyl-pyrimidine of m.p. 40°-43° C.