HCID 67348061, compound → HCID 11589857, compound

HRID 1992323Notes

Reaction equation

HRID 1992323 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[C:10][Si](C)(C)C)=[CH:5][N:4]=1.FC(F)(F)S(O[C:21]1[CH2:22][CH2:23][N:24]([S:27]([CH2:30][C:31]2([CH3:38])[C:35](=[O:36])[NH:34][C:33](=[O:37])[NH:32]2)(=[O:29])=[O:28])[CH2:25][CH:26]=1)(=O)=O>CN(C=O)C.[Cu]I.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>[CH3:38][C@:31]1([CH2:30][S:27]([N:24]2[CH2:23][CH:22]=[C:21]([C:10]#[C:9][C:6]3[CH:5]=[N:4][C:3]([S:2][CH3:1])=[N:8][CH:7]=3)[CH2:26][CH2:25]2)(=[O:29])=[O:28])[NH:32][C:33](=[O:37])[NH:34][C:35]1=[O:36]

Participants

6

Reactant 2

HCID 67348061HCID 67348061, compoundHCID 86642355HCID 86642355, compound

Product 1

HCID 11589857HCID 11589857, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

The title compound was prepared by the general method described by Nishihara et al., J. Org. Chem., 2000, 65, 1780-1787. To a solution of 2-(methylthio)-5-[(trimethylsilyl)ethynyl]pyrimidine (0.55 g, 2.47 mmol) and 1-{[(4-methyl-2,5-dioxoimidazolidin-4-yl)methyl]sulfonyl}-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate (0.94 g, 2.22 mmol) in DMF (5 mL) was added CuI (10 mol %) and PdCl2(PPh3)2 (5 mol %) and the mixture was heated at 85° C. for 6 hours. The mixture was partitioned between EtOAc (20 mL) and water (10 mL), and the aqueous layer was extracted three times with EtOAc. The combined organic layers were washed with brine, water and concentrated to a brown oil (1.6 g). The title compound was obtained as a solid (10 mg) following purification by preparative HPLC (using a Xterra-Prep-MS-C18 (50×19) column with a 12 minutes gradient 5-35% of acetonitrile in water with 0.06% NH3).

Workup

  1. customThe title compound was prepared by the general method
  2. customThe mixture was partitioned between EtOAc (20 mL) and water (10 mL)
  3. extractionthe aqueous layer was extracted three times with EtOAc
  4. washThe combined organic layers were washed with brine, water
  5. concentrationconcentrated to a brown oil (1.6 g)

Sources & evidence

ORD record
ord-83f92b84256b4270843774339086b0a5
Source dataset
uspto-grants-2010_01
Patent number
US07648992B2

Reaction notes

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