5-Bromo-2-iodopyrimidine → 5-bromo-2-ethenylpyrimidine

HRID 1752304Notes

Reaction equation

HRID 1752304 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[CH:9]([Mg]Br)=[CH2:10]>C1COCC1.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>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH:9]=[CH2:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 70066515-Bromo-2-iodopyrimidineHCID 178418507HCID 178418507, compound

Product 1

HCID 536286645-bromo-2-ethenylpyrimidineYield 86.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-iodopyrimidine (14.2 g, 50 mmol) and Pd(PPh3)4 (865 mg, 0.75 mmol) in THF (200 mL) at room temperature under nitrogen was added dropwise vinylmagnesium bromide (100 mL, 100 mmol, 1 M in THF). The reaction mixture was heated to reflux for 2 hours. The formed mixture was quenched with water (200 mL) and extracted with EtOAc (200 mL×3). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford an oil which was purified by preparative column chromatography to afford 5-bromo-2-vinylpyrimidine (8 g, yield: 86%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe formed mixture was quenched with water (200 mL)
  4. extractionextracted with EtOAc (200 mL×3)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford an oil which
  9. customwas purified by preparative column chromatography

Sources & evidence

ORD record
ord-4e8b313f704c4dddad1ca533f19ccd2e
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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