HCID 67348061, compound → HCID 11589857, compound

HRID 1669657Notes

Reaction equation

HRID 1669657 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-0786e4c13979459e99562dff0f854374
Source dataset
uspto-grants-2011_08
Patent number
US07989620B2

Reaction notes

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