Sodium Carbonate → 5-(Pyrimidin-2-yl)thiophene-2-carbaldehyde

HRID 2416518Notes

Reaction equation

HRID 2416518 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[S:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].Br[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1>O.COCCOC.ClCCl.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>[N:19]1[CH:20]=[CH:21][CH:22]=[N:23][C:18]=1[C:12]1[S:13][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 27734305-Formyl-2-thiopheneboronic acid

Product 1

HCID 226312225-(Pyrimidin-2-yl)thiophene-2-carbaldehydeYield 26%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of Na2CO3 (3.16 g) and 5-formyl-2-thiopheneboronic acid (2.4 g, 15.1 mmol) in water (15 mL) were added to a solution of 2-bromopyrimidine (2 g, 12.58 mmol) and tetrakis(triphenylphosphine)palladium(0) (480 mg, 0.46 mmol) in DME (30 mL) and the mixture was heated to reflux for 24 hr. The cooled reaction mixture was diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 1:1 hexane/ethyl acetate) yielded 620 mg (26%) of the title compound. MS 191 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 hr
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2ccbb49f0c1a4c61aefa69f3b819d0d0
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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