Potassium Carbonate → HCID 22340987, compound

HRID 1166045Notes

Reaction equation

HRID 1166045 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:17]([Cl:18])=[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[N:10]=2)=[CH:4][C:3]=1[OH:19].Cl[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC.CS(C)=O>[Cl:18][C:17]1[C:9]([C:5]2[CH:4]=[C:3]([O:19][C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:2]([Cl:1])=[CH:7][C:6]=2[F:8])=[N:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 15456859HCID 15456859, compound

Product 1

HCID 22340987HCID 22340987, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 22341001HCID 22341001, compoundSolvent

Procedure

To a solution of 2-chloro-5-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-4-fluorophenol (0.5 g) and 2-chloropyrimidine (0.25 g),in a mixed solvent of 2-butanone:dimethylsulfoxide (1:4) (50 ml) was added potassium carbonate (0.35 g) at room temperature. After addition, the mixture was heated at reflux for 12 hours under a nitrogen atmosphere. The mixture was allowed to cool to room temperature and partitioned between ethyl acetate and brine. The organic phase was washed with brine (×2) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluent, ethyl acetate:hexane, 2:1) to give the desired compound (0.47 g).

Workup

  1. additionAfter addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 12 hours under a nitrogen atmosphere
  4. custompartitioned between ethyl acetate and brine
  5. washThe organic phase was washed with brine (×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography on silica gel (eluent, ethyl acetate:hexane, 2:1)

Sources & evidence

ORD record
ord-11b54a2ad22c45be898ad809c2ce3cca
Source dataset
uspto-grants-2003_09
Patent number
US06613718B2

Reaction notes

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