Tributylvinyltin → 5-bromo-2-ethenylpyrimidine

HRID 1260239Notes

Reaction equation

HRID 1260239 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[CH2:9]([Sn](CCCC)(CCCC)C=C)[CH2:10]CC>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 81998TributylvinyltinHCID 70066515-Bromo-2-iodopyrimidine

Product 1

HCID 536286645-bromo-2-ethenylpyrimidineYield 68.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

5-Bromo-2-iodo-pyrimidine (9.15 g, 32.11 mmol) was dissolved in THF (150 ml) and Pd(PPh3)4 (18.85 g, 1.60 mmol) was added, followed by tributyl-vinyl-stannane (9.38 ml, 32.11 mmol). The resulting mixture was heated at 140° C. for 20 min under microwave irradiations, next filtered through a pad of celite and concentrated. The crude material was diluted with CH2Cl2 and washed with water. Separation of the layers, drying (Na2SO4) of the organic phase, filtration and evaporation in vacuo provided the crude material, which was purified by flash column chromatography (CH2Cl2) to give the title compound (4.05 g, 68%) as a volatile yellow oil crystallizing at 4° C.

Workup

  1. filtrationnext filtered through a pad of celite
  2. concentrationconcentrated
  3. additionThe crude material was diluted with CH2Cl2
  4. washwashed with water
  5. customSeparation of the layers
  6. customdrying
  7. filtration(Na2SO4) of the organic phase, filtration and evaporation in vacuo
  8. customprovided the crude material, which
  9. customwas purified by flash column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-094331f9b8fa4bc7a4868736108abfe6
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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