3-(Trifluoromethyl)aniline → 6-(2-nitro-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)phenyl)-pyrimidin-4-amine

HRID 1407972Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].Cl[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[C:23]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:22]=[CH:21][C:20]=2[N+:31]([O-:33])=[O:32])[N:16]=[CH:15][N:14]=1>CN(C=O)C.Cl>[N+:31]([C:20]1[CH:21]=[CH:22][C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:24][C:19]=1[C:17]1[N:16]=[CH:15][N:14]=[C:13]([NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[CH:18]=1)([O-:33])=[O:32]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 15 mg of 3-(trifluoromethyl)aniline and 27 mg intermediate 3.1b in 1 mL of DMF was treated with 1 drop of concentrated hydrochloric acid and heated to 90° C. for 1 h. The solution was cooled and partitioned between ethyl acetate and water. The organic extracts were washed with brine and dried over Na2SO4. The solvent was evaporated at reduced pressure to give 28 mg of product.

Workup

temperatureThe solution was cooled
custompartitioned between ethyl acetate and water
washThe organic extracts were washed with brine
dry with materialdried over Na2SO4
customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record: ord-b0229613549544569ba4a9b6350aa84b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916569B2

Reaction notes

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