Sodium Carbonate → 4-(2-Pyrimidinyl)-2-thiophenecarboxaldehyde

HRID 2416521Notes

Reaction equation

HRID 2416521 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[S:13][CH:12]=[C:11](B(O)O)[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:11]1[CH:10]=[C:9]([CH:7]=[O:8])[S:13][CH:12]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 110841152-Formylthiophene-4-boronic acid

Product 1

HCID 226312394-(2-Pyrimidinyl)-2-thiophenecarboxaldehyde

Reagents, catalysts & solvents 4

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

Procedure

A mixture of Na2CO3 (3.16 g) and 5-formyl-3-thiopheneboronic acid (2.4 g, 15.1 mmol) in water (15 mL) are 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 is heated to reflux for 24 hr. The cooled reaction mixture is diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography yields the title compound. MS 191 (M+H)+.

Workup

  1. temperaturethe mixture is 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

Sources & evidence

ORD record
ord-d7f48711a79e4e73b45a4d67aca7609a
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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