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

HRID 1928597Notes

Reaction equation

HRID 1928597 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-d62d34a3943f448791076a23e5876b69
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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