2-Fluoro-3-(tributylstannyl)pyrazine → HCID 66610755, compound

HRID 1621501Notes

Reaction equation

HRID 1621501 reaction equation
I[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[F:11][C:12]1[C:17]([Sn](CCCC)(CCCC)CCCC)=[N:16][CH:15]=[CH:14][N:13]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:12]1[C:17]([C:2]2[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=2)=[N:16][CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 121306622-Fluoro-3-(tributylstannyl)pyrazineHCID 601547162-Iodo-4-methyl-6-(methylthio)-1,3,5-triazine

Product 1

HCID 66610755HCID 66610755, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-iodo-4-methyl-6-(methylthio)-1,3,5-triazine (100 mg, 0.374 mmol), 2-fluoro-3-(tributylstannyl)pyrazine (145 mg, 0.374 mmol) and tetrakis(triphenylphosphine)palladium(0) (43.3 mg, 0.037 mmol) in toluene (2 mL) was stirred at 110° C. for 18 h. The mixture was cooled down to room temperature. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 40% EtOAc/hexanes to give 2-(3-fluoropyrazin-2-yl)-4-methyl-6-(methylthio)-1,3,5-triazine (42 mg, 0.177 mmol, 47.3% yield). 1H NMR (300 MHz, CDCl3) δ 8.73 (s, 1H); 8.42 (s, 1H); 2.73 (s, 3H); 2.65 (s, 3H). m/z (ESI, +ve ion) 238.0 (M+H)+.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-ac74f82261534f6dabceeb517794aa25
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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