Potassium Carbonate → HCID 86635372, compound

HRID 657150Notes

Reaction equation

HRID 657150 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6](Cl)[N:5]=[C:4](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][O:11][C:6]=2[N:5]=[C:4](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86635371HCID 86635371, compound

Product 1

HCID 86635372HCID 86635372, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-{4,6-dichloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}-1-propanol (275 mg, 0.89 mmol) in DMF (4 mL) was added K2CO3 (0.50 g, 3.6 mmol). The suspension was warmed to 60° C. and allowed to stir 16 h under nitrogen. The reaction was cooled to rt, concentrated to remove most of the DMF and the residue was partitioned between EtOAc and water. The aqueous layer was further extracted with EtOAc (2×), washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was then purified by column chromatography (silica gel) using an EtOAc/hexanes gradient to yield the desired compound as a yellow solid (0.21 g, 88%).

Workup

  1. temperatureThe reaction was cooled to rt
  2. concentrationconcentrated
  3. customto remove most of the DMF
  4. customthe residue was partitioned between EtOAc and water
  5. extractionThe aqueous layer was further extracted with EtOAc (2×)
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe crude residue was then purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-6048aab477da4479b344326c7e9782a7
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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