2,4-Difluoroaniline → HCID 9931756, compound

HRID 1264894Notes

Reaction equation

[CH3:1][C:2]1[C:3]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]2[CH3:20])=[N:4][C:5]([Cl:9])=[N:6][C:7]=1[CH3:8].[F:21][C:22]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:23]=1[NH2:24]>CS(C)=O.C(OCC)(=O)C>[ClH:9].[CH3:1][C:2]1[C:3]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]2[CH3:20])=[N:4][C:5]([NH:24][C:23]2[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:22]=2[F:21])=[N:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 120 °C

Procedure

To the solution of 5,6-dimethyl-2-chloro4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine (0.8 g, 2.78 mmol) in dimethyl sulfoxide (1.5 ml), was added 2,4-difluoroaniline (0.5 ml, 4.9 mmol). The reaction mixture was heated to 120° C., stirred for 2 hours, and cooled to room temperature. The resulting solution was diluted with ethyl acetate, washed with water and sodium hydroxide solution, and dried over anhydrous magnesium sulfate. The organic layer was concentrated in vacuo. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate/dichloromethane =⅕), and then treated with ethyl ether solution saturated with hydrochloric acid to afford 0.2 g (17%) of the titled compound.

Workup

temperaturecooled to room temperature
washwashed with water and sodium hydroxide solution
dry with materialdried over anhydrous magnesium sulfate
concentrationThe organic layer was concentrated in vacuo
additiontreated with ethyl ether solution saturated with hydrochloric acid

Sources & evidence

ORD record: ord-ca6a61412ea4453faa130f1a3c26aa56
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545008B1

Reaction notes

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