Triethylamine → HCID 9953738, compound

HRID 1264893Notes

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].C(N(CC)CC)C.[F:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[F:36])[NH2:32]>C(O)C(O)C.ClCCl>[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:32][C:31]2[CH:33]=[CH:34][C:35]([F:36])=[C:29]([F:28])[CH:30]=2)=[N:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 140 °C

Procedure

To the solution of 5,6-dimethyl-2-chloro4-(1-methyl- 1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine (0.5 g, 1.74 mmol) prepared in accordance with WO 96/05177 in propylene glycol (2 ml), were added triethylamine (0.3 ml, 2.09 mmol) and 3,4-difluoroaniline (0.2 ml, 2.09 mmol). The reaction mixture was heated to 140° C., stirred for 18 hours, and cooled to room temperature. The resulting solution was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate/hexane =⅓), and then treated with ethyl ether solution saturated with hydrochloric acid to afford 0.1 g (13.8%) of the titled compound.

Workup

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

Sources & evidence

ORD record: ord-0850bdd777aa4113a259bb9163984086
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545008B1

Reaction notes

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