Malonic Acid → 3-[2-(4-Fluoro-phenyl)-pyrimidin-5-yl]-acrylic Acid

HRID 1873769Notes

Reaction equation

HRID 1873769 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][C:11]([CH:14]=[CH:17][C:18]([OH:20])=[O:19])=[CH:12][N:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 140084722-(4-Fluorophenyl)pyrimidine-5-carbaldehyde

Product 1

HCID 687119093-[2-(4-Fluoro-phenyl)-pyrimidin-5-yl]-acrylic Acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

945 mg (4.67 mmol) of 2-(4-fluoro-phenyl)-pyrimidine-5-carbaldehyde, 1544 mg (14.84 mmol) of malonic acid and 4197 mg (49.29 mmol) of piperidine in 50 ml of pyridine were stirred at 125° C. for 17 h. After concentration, water and hydrochloric acid were added, and the solid product was filtered off with suction and dried. Yield: 1.01 g.

Workup

  1. concentrationAfter concentration, water and hydrochloric acid
  2. additionwere added
  3. filtrationthe solid product was filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-725e0039cfc64d37862b2ba614c32e8e
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Reaction notes

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