Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-Butyl 4-[(2-methylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate

HRID 1669665Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][Si](C)(C)C)=[CH:4][N:3]=1.FC(F)(F)S(O[C:20]1[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH:25]=1)(=O)=O>CN(C=O)C.Cl[Cu].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of CuCl (1 mg, 0.01 mmol) and PdCl2(PPh3)2 (0.003 g, 0.004 mmol) in DMF (2 mL) were added 2-methyl-5-[(trimethylsilyl)ethynyl]pyrimidine (0.088 g, 0.462 mmol) and tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (Example 2e) (0.183 g, 0.555 mmol) at room temperature. The reaction mixture was stirred for 8 h at 80° C. After cooling, the mixture was quenched with 1N HCl and extracted with ether (3×). The combined organic layers were washed with saturated aqueous NaHCO3 solution, brine and dried. Filtration and evaporation afforded a brown oil, which was purified on HPLC to give the subtitle compound (0.062 g, 45%).

Workup

temperatureAfter cooling
customthe mixture was quenched with 1N HCl
extractionextracted with ether (3×)
washThe combined organic layers were washed with saturated aqueous NaHCO3 solution, brine
customdried
filtrationFiltration and evaporation
customafforded a brown oil, which
customwas purified on HPLC

Sources & evidence

ORD record: ord-a72ee89f05634ebe82039c14c957b946
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989620B2

Reaction notes

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