Potassium Carbonate → HCID 57761386, compound

HRID 230972Notes

Reaction equation

HRID 230972 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1.[F:23][C:24]([F:38])([F:37])[C:25]1[C:26]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[N:27][CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O>[Cl:16][C:12]1[CH:11]=[C:10]([C:6]2[C:7]([C:8]#[N:9])=[C:2]([N:34]3[CH2:35][CH2:36][N:31]([C:26]4[C:25]([C:24]([F:38])([F:23])[F:37])=[CH:30][CH:29]=[CH:28][N:27]=4)[CH2:32][CH2:33]3)[N:3]=[C:4]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:5]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27777861-[3-(Trifluoromethyl)pyridin-2-yl]piperazineHCID 86610312HCID 86610312, compound

Product 1

HCID 57761386HCID 57761386, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Dissolve 4-chloro-6-(3-chlorophenyl)-2-morpholinopyrimidine-5-carbonitrile (33.5 mg, 0.1 mmoles) and 1-(3-(trifluoromethyl)-pyridin-2-yl)piperazine (23 mg, 0.1 mmoles) in CH3CN (1.0 mL) under nitrogen atmosphere. Add anhydrous powdered K2CO3 (28 mg, 0.2 mmoles) to this mixture and heat at 80° C. for 24 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 Purify by flash column chromatography using 30% EtOAc/hexane to afford the title product as white solid. NMR (DMSO-D6) δ 3.30 (4H, s), 3.62 (4H, m), 3.80 (4H, s), 3.93 (4H, s), 7.19 (1H, m), 7.51 (1H, m), 7.59 (1H, m), 7.76 (1H, m), 7.83 (1H, s), 8.07 (1H, d, J=2.0), 8.52 (1H, d, J=1.2). Mass spec m/z=530.12.

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-1b9e5a79e6b14668bbc93bc4c47c09ab
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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