Ethylamine → 6-Chloro-N-ethyl-5-nitro-2-(trifluoromethyl)pyrimidin-4-amine

HRID 597459Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=1.[CH2:16]([N:18](CC)CC)[CH3:17].C(N)C>C(O)C>[CH2:16]([NH:18][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=1)[CH3:17]

Participants

Conditions

Temperature: -30 °C

Procedure

5.25 g (0.02 mole) of 4,6 -dichloro-5-nitro-2-trifluoromethyl-pyrimidine are dissolved in 100 ml of absolute ethanol and the solution is cooled to -30° C. At this temperature 2.0 g (0.02 mole) of triethylamine as acid acceptor and 0.9 g (0.02 mole) of ethylamine are added. The mixture is stirred initially for 4 hours at -20° to -30° C and then for 6 hours at 0° C. After it has been left to stand overnight at 20° C, the reaction mixture is concentrated to dryness and the residue is taken up in water and washed with water. The ethereal phase is dried and concentrated to yield 5.3 g of 4-ethylamino-6-chloro-5-nitro-2-trifluoromethyl-pyrimidine as a pale yellow oil (nD20 : 1.4985).

Workup

waitfor 6 hours at 0° C
waitAfter it has been left
waitto stand overnight at 20° C
concentrationthe reaction mixture is concentrated to dryness
washwashed with water
customThe ethereal phase is dried
concentrationconcentrated

Sources & evidence

ORD record: ord-5cd581c062c64ce0a8ec2eef36181dc3
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04014677

Reaction notes

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