Tributylvinyltin → 5-bromo-2-ethenylpyrimidine

HRID 2262624Notes

Reaction equation

HRID 2262624 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-369cfdbfb63949b8a27fee8e454561e1
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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