Potassium Carbonate → HCID 58093422, compound

HRID 474999Notes

Reaction equation

HRID 474999 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[N:3]=1.[C:10]1(/[CH:16]=[CH:17]/B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:9][O:8][C:4]1[N:3]=[C:2](/[CH:17]=[CH:16]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5752304-Chloro-2-methoxypyrimidineHCID 5702628Styrylboronic acid

Product 1

HCID 58093422HCID 58093422, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 4-chloro-2-methoxypyrimidine (0.36 g, 2.5 mmol), trans-2-phenylvinylboronic acid (0.56 g, 3.8 mmol) and potassium carbonate (0.69 g, 5.0 mmol) in DMSO (8.0 mL) was purged with argon for 5 min. 1,1′-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.18 g, 0.25 mmol) was added to the above solution. The reaction mixture was purged with argon for 5 min and then heated at 95° C. for 16 h. The reaction solution was cooled to room temperature, diluted with ethyl acetate, washed with water (2×) and brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel hexanes/ethyl acetate 95:5 to 60:40) to afford the title compound (0.51 g, 96%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.47 (d, J=5.0 Hz, 1H), 7.92 (d, J=16.0 Hz, 1H), 7.61-7.58 (m, 2H), 7.42-7.35 (m, 3H), 7.01 (d, J=16.0 Hz, 1H), 6.94 (d, J=5.0 Hz, 1H), 4.07 (s, 3H).

Workup

  1. customThe reaction mixture was purged with argon for 5 min
  2. temperatureThe reaction solution was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washwashed with water (2×) and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography (silica gel hexanes/ethyl acetate 95:5 to 60:40)

Sources & evidence

ORD record
ord-ad06b1d8e04e43a796a92f981bb5e314
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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