4-Phenylpiperidine → HCID 18753235, compound

HRID 1838183Notes

Reaction equation

HRID 1838183 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1.C(N(C(C)C)C(C)C)C.[C:25]1([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[OH:13][CH2:12][CH2:11][NH:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([N:34]2[CH2:35][CH2:36][CH:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:32][CH2:33]2)[N:3]=[C:4]([S:14][CH3:15])[N:5]=1

Participants

5

Reactant 3

HCID 698734-PhenylpiperidineHCID 81531DiisopropylethylamineHCID 3361104HCID 3361104, compound

Product 1

HCID 18753235HCID 18753235, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.47 g (1.9 mmol) of 4-chloro-6-(2-hydroxy-ethylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile (Timkevicius, S., Chemija 1997, 1, 58-61) and 0.33 ml (1.9 mmol) of N-ethyl-diisopropylamine in 5 ml of dichloromethane was treated at 30° C. with 310 mg (1.9 mmol) of 4-phenyl-piperidine and stirred during 7 hours. For the working-up, the reaction mixture was evaporated under reduced pressure, and the residue obtained was directly chromatographed on silica gel using a 99:1 mixture of dichloromethane and methanol as the eluent yielding 490 mg (1.33 mmol, 70% of theory) of the 4-(2-hydroxy-ethylamino)-2-methylsulfanyl-6-(4-phenyl-piperidin-1-yl)-pyrimidine-5-carbonitrile as an amorphous, white solid; MS: [M+H]+=370.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customthe residue obtained
  3. customwas directly chromatographed on silica gel using
  4. additiona 99:1 mixture of dichloromethane and methanol as the eluent

Sources & evidence

ORD record
ord-ba8948b77fa84c398fdb64b860b28021
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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