Diisopropylethylamine → 4-Chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1838186Notes

Reaction equation

HRID 1838186 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.C(N(C(C)C)C(C)C)C.Cl.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1>O1CCOCC1>[Cl:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([N:33]2[CH2:34][CH2:35][CH:30]([C:27]3[CH:26]=[CH:25][C:24]([F:23])=[CH:29][CH:28]=3)[CH2:31][CH2:32]2)[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 42016204,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochloride

Product 1

HCID 187532704-Chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A dispersion of 0.5 g (2.3 mmol) of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile (J. Heterocycl. Chem. 1971, 8, 445-453) and 0.65 g (5.0 mmol) of N-ethyl-diisopropylamine in 40 ml of dioxane was treated at room temperature with 0.54 g (5.0 mmol) of 4-(4-fluorophenyl)-piperidine hydrochloride during 18 h. For the working-up, the reaction mixture was evaporated, and, thereafter, the residue obtained was directly chromatographed on silica gel using toluene as the eluent yielding 660 mg (1.8 mmol, 80% of theory) of 4-chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrile as an amorphous, white solid; MS: [M+H]+=363.

Workup

  1. customthe reaction mixture was evaporated
  2. customthe residue obtained
  3. customwas directly chromatographed on silica gel

Sources & evidence

ORD record
ord-127a232a201e4df0ba8422ba2b0d253b
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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