Potassium Carbonate → HCID 57761720, compound

HRID 230968Notes

Reaction equation

HRID 230968 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:3]=1.[F:22][C:23]([F:37])([F:36])[C:24]1[C:25]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:26][CH:27]=[CH:28][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.O>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[CH:7]=[C:2]([N:33]3[CH2:34][CH2:35][N:30]([C:25]4[C:24]([C:23]([F:37])([F:22])[F:36])=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:31][CH2:32]3)[N:3]=[C:4]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[N:5]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27777861-[3-(Trifluoromethyl)pyridin-2-yl]piperazineHCID 57761589HCID 57761589, compound

Product 1

HCID 57761720HCID 57761720, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Dissolve 4-chloro-6-(3-chloro-4-fluorophenyl)-2-(pyridin-4-yl)pyrimidine (64 mg, 0.2 mmoles) and 1-(3-(trifluoromethyl)-pyridin-2-yl)piperazine (46 mg, 0.2 mmoles) in DMA (2.0 mL) under nitrogen atmosphere. Add anhydrous powdered K2CO3 (55 mg, 0.4 mmoles) to this mixture and heat at 140° C. for 20 hours. Cool, dilute with water (5 mL), extract with EtOAc (3×2 mL) and dry over MgSO4. Filter, and concentrate under vacuum to afford crude product. Wash the crude product with Et2O (2.0 mL) to afford the title product as cream colored solid. NMR (CDCl3) δ 3.34 (4H, s), 3.99 (4H, s), 7.20 (1H, m), 7.47 (1H, s), 7.43 (1H, t), 8.09 (1H, d, J=2.0), 8.30 (2H, m), 8.35 (1H, m), 8.55 (2H, m), 8.70 (2H, m). Mass spec m/z=515.24.

Workup

  1. temperatureCool
  2. extractionextract with EtOAc (3×2 mL)
  3. dry with materialdry over MgSO4
  4. filtrationFilter
  5. concentrationconcentrate under vacuum
  6. customto afford crude product
  7. washWash the crude product with Et2O (2.0 mL)

Sources & evidence

ORD record
ord-df598dd2c52b4522b20324a54de51845
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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