Dichloromethane → 5-Ethyl-2-{4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidin-1-yl}-pyrimidine

HRID 1622250Notes

Reaction equation

HRID 1622250 reaction equation
C(N(C(C)C)C(C)C)C.Cl[C:11]1[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=1.[CH3:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[CH:31][C:32]3[O:36][CH:35]([CH:37]4[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)[CH2:34][C:33]=3[CH:43]=2)=[CH:25][CH:24]=1)(=[O:22])=[O:21].ClCCl>CN(C)C=O.O>[CH2:17]([C:14]1[CH:13]=[N:12][C:11]([N:40]2[CH2:41][CH2:42][CH:37]([CH:35]3[CH2:34][C:33]4[CH:43]=[C:29]([C:26]5[CH:27]=[CH:28][C:23]([S:20]([CH3:19])(=[O:22])=[O:21])=[CH:24][CH:25]=5)[CH:30]=[CH:31][C:32]=4[O:36]3)[CH2:38][CH2:39]2)=[N:16][CH:15]=1)[CH3:18]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 679732894-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine

Product 1

HCID 712083675-Ethyl-2-{4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidin-1-yl}-pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Ethyldiisopropylamine (50 μL) and 2-chloro-5-ethylpyrimidine (17 μL) are added to a solution of 4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine (50 mg) in N,N-dimethylformamide (1 mL) and the reaction mixture is stirred at 120° C. for 2 h. After cooling to room temperature over night, dichloromethane and water are added. The aqueous phase is separated and extracted with dichloromethane. The combined organic phases are washed with water, 10% NH4Cl solution, and brine, and dried over MgSO4. The solvent is evaporated and the residue is triturated with diethyl ether to give the title compound. LC (method 4): tR=1.26 min; Mass spectrum (ESI+): m/z=464 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature over night
  2. customThe aqueous phase is separated
  3. extractionextracted with dichloromethane
  4. washThe combined organic phases are washed with water, 10% NH4Cl solution, and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent is evaporated
  7. customthe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-22183141dbed4968973ad7e52068ff5b
Source dataset
uspto-grants-2014_07
Patent number
US08778926B2

Reaction notes

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