Dimethylformamide → 2-{6-[3-(pyridin-3-yl)-1H-pyrazol-1-yl]pyridin-2-yl}pyrimidine

HRID 705035Notes

Reaction equation

CN(C=O)C.[NH:6]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:7]1.Br[C:18]1[N:23]=[C:22]([C:24]2[N:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].O>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[CH:9]=[CH:10][N:6]([C:18]3[N:23]=[C:22]([C:24]4[N:25]=[CH:26][CH:27]=[CH:28][N:29]=4)[CH:21]=[CH:20][CH:19]=3)[N:7]=2)[CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

10 ml of DMF were added to 515.5 mg (3.55 mmol) of 3-(1H-pyrazol-3-yl)pyridine (preparation cf. WO 94/29300 A1), 838.5 mg (3.55 mmol) of 2-(6-bromopyridin-2-yl)pyrimidine (WO 2010/006713), 28.2 mg (0.35 mmol) of copper(II) oxide, 2.31 g (7.10 mmol) of cesium carbonate and 276.3 mg (1.06 mmol) of iron(III) acetylacetonate, and the mixture was stirred at 90° C. for 60 hours. The entire reaction mixture was then cooled to room temperature, and water was added. The reaction mixture was then extracted with ethyl acetate. The organic phase was separated off, dried and concentrated under reduced pressure. The residue was purified by chromatography on silica gel. This gave 334 g (31.3% of theory) of 2-{6-[3-(pyridin-3-yl)-1H-pyrazol-1-yl]pyridin-2-yl}pyrimidine.

Workup

customThe entire reaction mixture
temperaturewas then cooled to room temperature
extractionThe reaction mixture was then extracted with ethyl acetate
customThe organic phase was separated off
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-a21d54091af042b5a1f92428a73479d4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173396B2

Reaction notes

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