Triphenylphosphine → HCID 59486242, compound

HRID 710570Notes

Reaction equation

HRID 710570 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([Sn](CCCC)(CCCC)CCCC)[N:6]=[CH:5][N:4]=1.[Cl:22][C:23]1[C:28](Cl)=[N:27][CH:26]=[CH:25][N:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[Cl:22][C:23]1[C:28]([C:7]2[CH:8]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][N:6]=2)=[N:27][CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 785752,3-DichloropyrazineHCID 59486262HCID 59486262, compound

Product 1

HCID 59486242HCID 59486242, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-methylsulfanyl-6-tributylstannanyl-pyrimidine (1.80 g, 4.33 mmol), 2,3-dichloro-pyrazine (1.94 g, 13 mmol), triphenylphosphine (0.907 g, 3.46 mmol), palladium (II) acetate (194 mg, 0.866 mmol) and dioxane (15 mL) was degassed and sealed in a pressure tube. After stirring at 120° C. for 16 h, the reaction mixture was concentrated, and the residue purified by silica gel flash chromatography (10% to 30% ethyl acetate in hexanes as eluant) to afford the title compound. 1H NMR 300 MHz (CDCl3) δ 9.10 (s, 1H), 8.64 (d, J=2 Hz, 1H), 8.29 (d, J=2 Hz, 1H), 7.70 (s, 1H), 2.64 (s, 3H).

Workup

  1. customwas degassed
  2. customsealed in a pressure tube
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue purified by silica gel flash chromatography (10% to 30% ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-9ec43752ca884660a8a88a37156c62e5
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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