Hydrochloric Acid → 5-Fluoropyrimidine-2-carbaldehyde

HRID 415447Notes

Reaction equation

HRID 415447 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([C:8]#N)=[N:6][CH:7]=1.CC(C[AlH]CC(C)C)C.C[OH:20].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[N:4][C:5]([CH:8]=[O:20])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 441818675-Fluoropyrimidine-2-carbonitrile

Product 1

HCID 534081435-Fluoropyrimidine-2-carbaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-fluoropyrimidine-2-carbonitrile (Method 6, 1.0 g, 8.1 mmol) in anhydrous THF at −78° C. was added a solution of DIBAL-H (8.1 mL) over a period of 20 minutes. The resulting mixture was stirred at this temperature for 2 hours whereupon MeOH was added. The solution was allowed to warm to room temperature whereupon a solution of conc. HCl was added. The resulting mixture was stirred for 2 hours at ambient temperature and the aqueous layer was washed with EtOAc (3×). The combined organic extracts were washed with brine and dried (MgSO4). Evaporation of the solvent afforded the titled compound (780 mg, 76%). MS: [M+H]+ 127.

Workup

  1. additionwas added
  2. additionwas added
  3. washthe aqueous layer was washed with EtOAc (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-13754ccb08da40bb88751de672b77625
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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