Dimethylformamide → 2,4-Dichloropyrimidine-5-carbaldehyde

HRID 750482Notes

Reaction equation

HRID 750482 reaction equation
Br[C:2]1[C:3]([Cl:9])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C([Mg]C(C)C)(C)C.[Cl-].CN([CH:21]=[O:22])C>C1COCC1>[Cl:8][C:5]1[N:4]=[C:3]([Cl:9])[C:2]([CH:21]=[O:22])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 178461730HCID 178461730, compound

Product 1

HCID 189831682,4-Dichloropyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-35 °C

Procedure

To a stirred solution of 5-bromo-2,4-dichloropyrimidine (Aldrich, 454 mg, 2 mmol) in THF at −78° C., diisopropyl magnesium chloride (2M solution in THF, 2.1 mmol, 1.05 mL) was added and the mixture was stirred for 30 minutes at −35° C. Next, the solution was cooled to −78° C. and 1 mL of dry DMF was added. The mixture was stirred for 120 minutes at −78° C. and the reaction was quenched with 1 N HCl. The mixture was extracted with EtOAc and dried with sodium sulfate. The solvent was removed and the residue was chromatographed to give a brown solid. 102 mg, 28%. H1NMR (CDCl3), δ (ppm), 9.0 (s, 1 H), 10.4 (s, 1 H).

Workup

  1. temperatureNext, the solution was cooled to −78° C.
  2. stirringThe mixture was stirred for 120 minutes at −78° C.
  3. customthe reaction was quenched with 1 N HCl
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialdried with sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was chromatographed
  8. customto give a brown solid

Sources & evidence

ORD record
ord-fc110678c122460abbd69646b44df370
Source dataset
uspto-grants-2008_07
Patent number
US07405220B2

Reaction notes

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