Potassium Carbonate → HCID 83824282, compound

HRID 528626Notes

Reaction equation

HRID 528626 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=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:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 783445-BromopyrimidineHCID 2773294(2-Bromophenyl)boronic acid

Product 1

HCID 83824282HCID 83824282, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromopyrimidine (500 mg, 3.14 mmol, Aldrich), (2-bromophenyl)boronic acid (947 mg, 4.71 mmol, Aldrich), Pd(PPh3)4 (363 mg, 0.314 mmol, GLR) and potassium carbonate (2.17 g, 15.7 mmol, Qualigens) in 1,4-dioxane:water (5.8 mL:2.9 mL) was degassed for 10 min. The reaction mixture was subjected to microwave heating for 30 minutes at 100° C. After completion, the reaction mixture was diluted with water (10 mL) and ethyl acetate (25 mL). The layers were separated. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 15% ethyl acetate in hexane) to get 5-(2-bromophenyl)pyrimidine (400 mg, 30.5%) as yellow solid. 1H NMR (400 MHz, CDCl3) δ 9.24 (s, 1H), 8.83 (s, 2H), 7.73 (d, J=7.9 Hz, 1H), 7.48-7.42 (m, 1H), 7.33 (d, J=7.4 Hz, 2H); MS (ESI, positive ion) m/z: 234.98 (M+1).

Workup

  1. customwater (5.8 mL:2.9 mL) was degassed for 10 min
  2. additionAfter completion, the reaction mixture was diluted with water (10 mL) and ethyl acetate (25 mL)
  3. customThe layers were separated
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain crude material which
  7. customwas purified by combiflash column chromatography (column size: 12 g; elution: 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ee59c652bdf54531972d2618a299980e
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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