Sodium Hydroxide → (4-Pyridin-4-yl-pyrimidin-2-yl)-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-amine

HRID 440874

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=O.[N+]([O-])(O)=O.[F:18][C:19]([F:34])([O:23][C:24]1[CH:25]=[C:26]([NH:30][C:31]([NH2:33])=[NH:32])[CH:27]=[CH:28][CH:29]=1)[CH:20]([F:22])[F:21].[OH-].[Na+]>C(O)C(C)C>[F:18][C:19]([F:34])([O:23][C:24]1[CH:25]=[C:26]([NH:30][C:31]2[N:33]=[C:5]([C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][N:32]=2)[CH:27]=[CH:28][CH:29]=1)[CH:20]([F:21])[F:22]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 13.2 g (75 mmol) of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one [described in EP-A-0 233 461] in 500 ml of isobutanol are added 23.6 g (75 mmol) of 3-(1,1,2,2-tetrafluoroethoxy)phenylguanidine nitrate. Following the addition of 4 g (100 mmol) of sodium hydroxide, the reaction mixture is stirred for 3 hours at 110° C. The suspension is concentrated under reduced pressure, the residue is dissolved in 500 ml of methylene chloride/tetrahydrofuran (1:1), and the solution is extracted with 300 ml of water. The organic phase is dried over sodium sulfate and concentrated on a rotovap. Recrystallisation from diethyl ether/tetrahydrofuran gives N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(4-pyridyl)-2-pyrimidine-amine; Rf =0.9 (methylene chloride:methanol =9:1), FAB-MS: 365 (M+ +1), m.p. 191°-192°.

Workup

concentrationThe suspension is concentrated under reduced pressure
dissolutionthe residue is dissolved in 500 ml of methylene chloride/tetrahydrofuran (1:1)
extractionthe solution is extracted with 300 ml of water
dry with materialThe organic phase is dried over sodium sulfate
concentrationconcentrated on a rotovap
customRecrystallisation from diethyl ether/tetrahydrofuran

Sources & evidence

ORD record: ord-6d720e076e314b5c9a8896caa32adf55
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05521184

Linked notes

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