Toluene → 5-Bromo-2-(2-methylpyridin-4-yl)pyrimidine

HRID 592199Notes

Reaction equation

HRID 592199 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[CH3:9][C:10]1[CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=[CH:12][N:11]=1.C([O-])([O-])=O.[Na+].[Na+].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.C(O)C.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:14]2[CH:13]=[CH:12][N:11]=[C:10]([CH3:9])[CH:15]=2)=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 70066515-Bromo-2-iodopyrimidineHCID 164142742-Methylpyridine-4-boronic acid pinacol ester

Product 1

HCID 584476465-Bromo-2-(2-methylpyridin-4-yl)pyrimidine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a sealed tube were added 5-bromo-2-iodopyrimidine 183-1 (114 mg, 0.4 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 183-2 (88 mg, 0.4 mmol), Pd(PPh3)4 (23 mg, 0.02 mmol), Na2CO3 (170 mg, 1.6 mmol), toluene (0.4 mL), H2O (0.4 mL) and ethanol (0.1 mL). The reaction mixture was stirred at 100° C. for 10 hours. After cooling to room temperature, the solvents were evaporated and the residue was redissolved in water (3 ml) and extracted with ethyl acetate (5 mL×3). The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by silica gel flash chromatography and eluted with 20% ethyl acetate in hexane to give 5-bromo-2-(2-methylpyridin-4-yl)pyrimidine 183-3. MS m/z 250.0 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvents were evaporated
  3. dissolutionthe residue was redissolved in water (3 ml)
  4. extractionextracted with ethyl acetate (5 mL×3)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel flash chromatography
  8. washeluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-eb24997dea334f2e9cc7a308c004e186
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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