Potassium Carbonate → 5-Bromo-2-(2-fluorophenyl)pyrimidine

HRID 42024

Reaction equation

HRID 42024 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 70066515-Bromo-2-iodopyrimidine

Product 1

HCID 497586955-Bromo-2-(2-fluorophenyl)pyrimidineYield 71.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-bromo-2-iodopyrimidine (2.58 mmol, 0.500 g), 2-fluorophenylboronic acid (3.87 mmol, 0.542 g), 2M aqueous solution of K2CO3 (7.76 mmol, 3.9 ml), Pd(PPh3)4 in dioxane (12 ml) was heated at 110° C. overnight. The solvent was evaporated and the solid residue was extracted between water and ethyl acetate. The organic phase was evaporated and the crude residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 0.466 g (yield 56%) of the expected product.

Workup

  1. customThe solvent was evaporated
  2. extractionthe solid residue was extracted between water and ethyl acetate
  3. customThe organic phase was evaporated
  4. customthe crude residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-db65dc6d4e8a4422803c0cb854df8532
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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