Potassium Carbonate → HCID 86623130, compound

HRID 1926716Notes

Reaction equation

HRID 1926716 reaction equation
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([OH:10])=[CH:6][N:5]=2)[CH2:3][CH2:2]1.F[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([O:10][C:12]3[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=3)=[CH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 198710372-Cyclopropylpyrimidin-5-ol

Product 1

HCID 86623130HCID 86623130, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Cyclopropylpyrimidin-5-ol (0.272 g, 2.0 mmol), 4-fluorobenzaldehyde (0.22 mL, 2.1 mmol) and potassium carbonate (0.414 g, 3.0 mmol) in dry DMF (2.0 mL) were heated to 120° C. in a sealed tube for 3 hours. The slurry was diluted with water and extracted twice with EtOAc. The combined organic phases were washed three times with water and brine, dried, filtered and concentrated to give a yellow oil. Purification by column chromatography using 20 g silica and a gradient of 0% to 50% EtOAc-heptanes as eluent gave 0.478 g (99% yield) of the subtitle compound as a colourless oil.

Workup

  1. extractionextracted twice with EtOAc
  2. washThe combined organic phases were washed three times with water and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-c7862ba76660490684ce4124e73f4782
Source dataset
uspto-grants-2012_05
Patent number
US08183251B2

Reaction notes

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