4-Piperidineethanol → 2-(2-Ethoxybenzyl)-4-[4-(2-hydroxyethyl)-1-piperidinyl]-6-oxo-1,6-dihydro-5-pyrimidine-carbonitrile

HRID 414962Notes

Reaction equation

HRID 414962 reaction equation
[CH2:1]([O:3][C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][C:7]1[NH:8][C:9](=[O:17])[C:10]([C:15]#[N:16])=[C:11](SC)[N:12]=1)[CH3:2].[NH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]1>C(#N)C>[CH2:1]([O:3][C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][C:7]1[NH:8][C:9](=[O:17])[C:10]([C:15]#[N:16])=[C:11]([N:22]2[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]2)[N:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 739534-PiperidineethanolHCID 584079112-(2-Ethoxybenzyl)-4-(methylsulphanyl)-6-oxo-1,6-dihydro-5-pyrimidinecarbonitrile

Product 1

HCID 1359951092-(2-Ethoxybenzyl)-4-[4-(2-hydroxyethyl)-1-piperidinyl]-6-oxo-1,6-dihydro-5-pyrimidine-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.1 g (0.37 mmol) of 2-(2-ethoxybenzyl)-4-(methylsulphanyl)-6-oxo-1,6-dihydro-5-pyrimidinecarbonitrile is heated with 0.13 g (0.99 mmol) of 2-(4-piperidinyl)ethan-1-ol in 3 ml of acetonitrile at 90° C. under argon for five days. After cooling to room temperature, the crude product is purified by preparative HPLC. 45 mg (43% of theory) of the title compound are obtained as a colourless solid.

Workup

  1. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-3c7e7b0e2cf54d5c8f026a89132cbed0
Source dataset
uspto-grants-2012_01
Patent number
US08088769B2

Reaction notes

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