Sodium Carbonate → (2E)-3-[4-(5-bromo-2-pyrimidinyl)phenyl]-2-propen-1-ol

HRID 2416541Notes

Reaction equation

HRID 2416541 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[Br:7][C:8]1[CH:9]=[N:10][C:11](I)=[N:12][CH:13]=1.[OH:15][CH2:16]/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.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:7][C:8]1[CH:9]=[N:10][C:11]([C:22]2[CH:23]=[CH:24][C:19](/[CH:18]=[CH:17]/[CH2:16][OH:15])=[CH:20][CH:21]=2)=[N:12][CH:13]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 70066515-Bromo-2-iodopyrimidineHCID 22630844[4-[(1E)-3-hydroxy-1-propenyl]phenyl]boronic Acid

Product 1

HCID 22631131(2E)-3-[4-(5-bromo-2-pyrimidinyl)phenyl]-2-propen-1-olYield 18%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 M aq. Na2CO3 (2 mL) was added to a mixture of 5-bromo-2-iodopyrimidine (0.57 g, 2.00 mmol), Pd(Ph3P)4 (23 mg, 0.020 mmol), and [4-[(1E)-3-hydroxy-1-propenyl]phenyl]boronic acid (360 mg, 2.02 mmol, prepared as described in Reference Example 238) in toluene (5 mL) and the resulting mixture was heated to reflux for 24 h. The cooled reaction mixture was diluted with ethyl acetate (20 mL) and the organic layer was separated, washed with brine (10 mL), dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 3:1 hexane/ethyl acetate) provided 104 mg (18%) of the title compound as a yellow solid. MS 291, 293 (M+H)+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 24 h
  3. customThe cooled reaction mixture
  4. customthe organic layer was separated
  5. washwashed with brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by chromatography (SiO2, 3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0ad99f6dfe4145fb82c5805083372a9f
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

Loading…