Potassium Carbonate → HCID 57761114, compound

HRID 230967Notes

Reaction equation

HRID 230967 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]([CH:16]([CH3:18])[CH3:17])[N:3]=1.[F:19][C:20]([F:34])([F:33])[C:21]1[C:22]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[N:23][CH:24]=[CH:25][CH:26]=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:30]3[CH2:31][CH2:32][N:27]([C:22]4[C:21]([C:20]([F:34])([F:19])[F:33])=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:28][CH2:29]3)[N:3]=[C:4]([CH:16]([CH3:18])[CH3:17])[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 57761908HCID 57761908, compound

Product 1

HCID 57761114HCID 57761114, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Dissolve 4-chloro-6-(3-chloro-4-fluorophenyl)-2-isopropyl-pyrimidine (56 mg, 0.2 mmoles) and 1-(3-(trifluoromethyl)-pyridin-2-yl)piperazine (46 mg, 0.2 mmoles) in DMA (1.5 mL) under nitrogen atmosphere. Add anhydrous powdered K2CO3 (55 mg, 0.4 mmoles) to this mixture and heat at 120° C. for 18 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 and purify by flash column chromatography using 7% EtOAc/hexane to afford the title product as colorless viscous oil. NMR (CDCl3) δ 1.33 (6H, d, J=1.8), 3.05 (1H, m), 3.40 (4H, m), 3.87 (4H, m), 6.68 (1H, s), 7.03 (1H, m), 7.19 (1H, t), 7.89 (2H, m), 8.07 (1H, d, J=2.3), 8.45 (1H, m). Mass spec m/z=480.22.

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. custompurify by flash column chromatography

Sources & evidence

ORD record
ord-09d2570563034c47a1f396f7a8799d1c
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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