Cesium carbonate → HCID 86711914, compound

HRID 1475219Notes

Reaction equation

HRID 1475219 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[N:8]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:29][C:30]1[N:35]=[C:34]([CH2:36]Cl)[CH:33]=[CH:32][N:31]=1>CN(C=O)C>[Cl:29][C:30]1[N:35]=[C:34]([CH2:36][N:6]2[C:2]([CH3:1])=[N:3][C:4]([C:7]3[O:11][N:10]=[C:9]([C:12]4[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=4)[N:8]=3)=[N:5]2)[CH:33]=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 216981282-Chloro-4-(chloromethyl)pyrimidineHCID 867118775-(5-methyl-1H-1,2,4-triazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Product 1

HCID 86711914HCID 86711914, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(5-Methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (200 mg, 0.643 mmol) was placed in DMF (5 ml) and Cs2CO3 (251 mg, 0.771 mmol) was added. The reaction was stirred for 5 min and 2-chloro-4-(chloromethyl)pyrimidine (126 mg, 0.771 mmol) was added. The reaction was stirred at 45° C. overnight and then partitioned between H2O (50 mL) and EtOAc (50 mL). The organic layer was separated, washed with H2O (2×50 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product which was purified by silica gel chromatography (EtOAc/Hexane 10%-100% EtOAc) to afford the desired compound as an orange solid (193 mg, 68%). MS (ES+) C17H11ClF3N7O2 requires: 437, 439. found 438, 440 [M+H]+; 1H NMR (600 MHz, DMSO-d6) δ 8.81 (d, J=5.1 Hz, 1H), 8.21 (d, J=8.7 Hz, 2H), 7.61 (d, J=8.7 Hz, 2H), 7.52 (d, J=5.1 Hz, 1H), 5.81 (s, 2H), 2.59 (s, 3H).

Workup

  1. stirringThe reaction was stirred at 45° C. overnight
  2. custompartitioned between H2O (50 mL) and EtOAc (50 mL)
  3. customThe organic layer was separated
  4. washwashed with H2O (2×50 mL) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the crude product which
  9. customwas purified by silica gel chromatography (EtOAc/Hexane 10%-100% EtOAc)

Sources & evidence

ORD record
ord-4f6ab8dec84e4b258b30756044578312
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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