2-(Piperidin-4-yloxy)pyrimidine → HCID 68694916, compound

HRID 1989760Notes

Reaction equation

HRID 1989760 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:3]=1.[NH:34]1[CH2:39][CH2:38][CH:37]([O:40][C:41]2[N:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[CH2:36][CH2:35]1>C1COCC1.CCOC(C)=O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([N:34]4[CH2:35][CH2:36][CH:37]([O:40][C:41]5[N:42]=[CH:43][CH:44]=[CH:45][N:46]=5)[CH2:38][CH2:39]4)(=[O:22])=[O:21])[CH:15]=3)[N:9]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 38367322-(Piperidin-4-yloxy)pyrimidineHCID 866154503-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonyl chloride

Product 1

HCID 68694916HCID 68694916, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonyl chloride (example I.2) (0.200 g, 0.409 mmol) by treatment with commercially available 2-(piperidin-4-yloxy)-pyrimidine [CAS-no. 499240-48-1] (0.367 g, 2.05 mmol) in THF (5 mL) at 23° C. for 16 h. Diluted with EtOAc, washed with 5% citric acid, sat. NaHCO3-sol. and brine, dried organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product, which was purified by silica gel column chromatography with EtOAc followed by trituration with diethyl ether/heptane to give the title compound (0.140 g, 54%) as a white foam. MS (ISP) 632.3 [(M+H)+]; mp 134° C. (dec.).

Workup

  1. washwashed with 5% citric acid, sat. NaHCO3-sol
  2. customRemoval of the solvent in vacuum
  3. waitleft a crude product, which
  4. customwas purified by silica gel column chromatography with EtOAc

Sources & evidence

ORD record
ord-2bb49a9cebf04ca78428ac4a6cd6ddf4
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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