Potassium Carbonate → HCID 59643068, compound

HRID 2251087Notes

Reaction equation

HRID 2251087 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]2[C:13]([CH:14]=O)=[CH:12][N:11]=[C:10]([S:16][CH3:17])[N:9]=2)=[CH:5][C:4]([CH3:18])=[N:3]1.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])=[O:22].C(=O)([O-])[O-].[K+].[K+].N12CCCN=C1CCCCC2>CN(C=O)C.CCOC(C)=O.[NH4+].[Cl-]>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21]([C:20]1[N:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([CH3:18])[CH:5]=2)[C:8]2[N:9]=[C:10]([S:16][CH3:17])[N:11]=[CH:12][C:13]=2[CH:14]=1)=[O:22]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27357852-Bromo-2'-chloroacetophenoneHCID 59643093HCID 59643093, compound

Product 1

HCID 59643068HCID 59643068, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 4-(2,5-dimethyl-2H-pyrazol-3-ylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde, 18, (0.25 g, 0.95 mmol) in DMF (4 mL) is added 2-bromo-1-(2-chloro-phenyl)-ethanone (0.33 g, 1.42 mmol) and potassium carbonate (0.26 g, 1.90 mmol). The reaction mixture is stirred at room temp for 21 hours after which the reaction solution is diluted with EtOAc and washed three times with aqueous saturated NH4Cl. The organic phase is washed with brine, dried (MgSO4), filtered, concentrated in vacuo and the resulting residue is dissolved in DMF (6 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.28 mL, 1.90 mmol) is added to the reaction. After stirring the reaction at room temp for 3 hours, the mixture is diluted with aqueous saturated NH4Cl solution and extracted with EtOAc. The organic phase is washed with brine, dried (MgSO4), filtered, concentrated in vacuo, and the resulting residue is purified over silica (33% EtOAc//hexanes) to afford 0.14 g of the desired product: 1H NMR (300 MHz, CDCl3) δ 8.92 (s, 1H), 7.52-7.35 (m, 4H), 7.00 (s, 1H), 6.14 (s, 1H), 3.67 (s, 3H), 2.55 (s, 3H), 2.37 (s, 3H); ESI+ MS: m/z (rel intensity) 398.0 (100, M++H).

Workup

  1. washwashed three times with aqueous saturated NH4Cl
  2. washThe organic phase is washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionthe resulting residue is dissolved in DMF (6 mL)
  7. stirringAfter stirring
  8. customthe reaction at room temp for 3 hours
  9. extractionextracted with EtOAc
  10. washThe organic phase is washed with brine
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customthe resulting residue is purified over silica (33% EtOAc//hexanes)

Sources & evidence

ORD record
ord-423bb7b1c18b46cdab06be425836fb59
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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