Ethanolamine → 4-[4-(4-Fluoro-phenyl)-piperidin-1-yl]-6-(2-hydroxy-ethylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1838187Notes

Reaction equation

HRID 1838187 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[N:5]=[C:4]([S:23][CH3:24])[N:3]=1.C(N(C(C)C)C(C)C)C.[CH2:34]([CH2:36][NH2:37])[OH:35]>O1CCOCC1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:6]3[C:7]([C:8]#[N:9])=[C:2]([NH:37][CH2:36][CH2:34][OH:35])[N:3]=[C:4]([S:23][CH3:24])[N:5]=3)[CH2:11][CH2:12]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 187532704-Chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 187532434-[4-(4-Fluoro-phenyl)-piperidin-1-yl]-6-(2-hydroxy-ethylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrileYield 83.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A dispersion of 200 mg (0.55 mmol) of 4-chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrile and 84 mg (0.6 mmol) of N-ethyl-diisopropylamine in 4 ml of dioxane was treated at 65° C. with 37 mg (0.6 mmol) of ethanolamine during 18 h. For the working-up, the reaction mixture was evaporated, and, thereafter, the residue obtained was directly chromatographed on silica gel using a 5:1 mixture of toluene and ethyl acetate as the eluent yielding 177 mg (0.46 mmol, 83% of theory) of the 4-[4-(4-fluoro-phenyl)-piperidin-1-yl]-6-(2-hydroxy-ethylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile as a yellowish oil which crystallized on standing. MS: [M+H]+=388.

Workup

  1. customthe reaction mixture was evaporated
  2. customthe residue obtained
  3. customwas directly chromatographed on silica gel using
  4. additiona 5:1 mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-bed19e6c98c946bea3fef4d068be7e03
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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