Triphenylphosphine → HCID 59486242, compound

HRID 912554Notes

Reaction equation

HRID 912554 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[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 (4) (1.80 g, 4.33 mmol), 2,3-dichloro-pyrazine (1.94 g, 13 mmol), PPh3 (0.907 g, 3.46 mmol) and palladium (II) acetate (194 mg, 0.866 mmol) in dioxane (15 mL) is degassed and sealed in a pressure tube. After stirring at 120° C. for 16 h, the reaction mixture is evaporated and purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 10% to 30% to afford the desired product 4-(3-chloro-pyrazin-2-yl)-6-methylsulfanyl-pyrimidine (37).

Workup

  1. customis degassed
  2. customsealed in a pressure tube
  3. customthe reaction mixture is evaporated
  4. custompurified by silica gel flash chromatography
  5. washeluting with ethyl acetate in hexanes from 10% to 30%

Sources & evidence

ORD record
ord-a157cd40c1a3459fae08835418cef8f0
Source dataset
uspto-grants-2011_09
Patent number
US08026243B2

Reaction notes

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