Potassium Carbonate → 5-Ethyl-2-{4-[3-(2-fluoro-4-methanesulfonyl-phenoxymethyl)-[1,2,4]triazol-1-yl]-piperidin-1-yl}-pyrimidine

HRID 80646Notes

Reaction equation

HRID 80646 reaction equation
Cl.[F:2][C:3]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:19]=[CH:18][C:4]=1[O:5][CH2:6][C:7]1[N:11]=[CH:10][N:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:33]1[N:38]=[CH:37][C:36]([CH2:39][CH3:40])=[CH:35][N:34]=1>CN(C)C=O>[CH2:39]([C:36]1[CH:35]=[N:34][C:33]([N:15]2[CH2:16][CH2:17][CH:12]([N:9]3[CH:10]=[N:11][C:7]([CH2:6][O:5][C:4]4[CH:18]=[CH:19][C:20]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:21][C:3]=4[F:2])=[N:8]3)[CH2:13][CH2:14]2)=[N:38][CH:37]=1)[CH3:40]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 35727632-Chloro-5-ethylpyrimidineHCID 687280424-[3-(2-Fluoro-4-methanesulfonyl-phenoxymethyl)-[1,2,4]triazol-1-yl]-piperidine hydrochloride2×

Product 1

HCID 251760355-Ethyl-2-{4-[3-(2-fluoro-4-methanesulfonyl-phenoxymethyl)-[1,2,4]triazol-1-yl]-piperidin-1-yl}-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-[3-(2-fluoro-4-methanesulfonyl-phenoxymethyl)-[1,2,4]triazol-1-yl]-piperidine hydrochloride salt (Intermediate 6, 0.100 g, 0.256 mmol), potassium carbonate (0.106 g, 0.768 mmol) and 2-chloro-5-ethyl-pyrimidine (0.062 mL, 0.512 mmol) in dimethylformamide (2 mL) was heated at 90° C. for 4 hours or until the starting material was consumed. The reaction was cooled to room temperature, the solution was diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over sodium sulfate, filtered and concentration in vacuo. The residue was chromatographed on silica gel (1:1 Hex/EtOAc) to afford the desired product. 1H NMR (CDCl3): δ 8.22 (2H, s), 8.17 (1H, s), 7.68 (2H, m), 7.38 (1H, m), 5.28 (2H, s), 4.92 (2H, d), 4.47 (1H, m), 3.08 (3H, s), 2.94 (2H, m), 2.48 (2H, q), 2.27 (1H, m), 2.18 (1H, m), 1.98 (2H, m), 1.20 (3H, t).

Workup

  1. customwas consumed
  2. temperatureThe reaction was cooled to room temperature
  3. additionthe solution was diluted with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentration in vacuo
  10. customThe residue was chromatographed on silica gel (1:1 Hex/EtOAc)

Sources & evidence

ORD record
ord-ef37e9df38a845068b9d4c30e31964a8
Source dataset
uspto-grants-2014_09
Patent number
US08846675B2

Reaction notes

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