1-(4-Fluorophenyl)piperazine → 4-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile

HRID 1838145Notes

Reaction equation

HRID 1838145 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]([NH:14][CH2:15][CH2:16][OH:17])[N:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[F:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:2]3[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[N:5]=[C:4]([NH:14][CH2:15][CH2:16][OH:17])[N:3]=3)[CH2:27][CH2:26]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 752601-(4-Fluorophenyl)piperazineHCID 81531DiisopropylethylamineHCID 187532174-Chloro-2,6-bis[(2-hydroxyethyl)amino]pyrimidine-5-carbonitrile

Product 1

HCID 187532364-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to the procedure described in example 20b, 4-chloro-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile was treated with the 1-(4-fluorophenyl)-piperazine in dioxane in the presence of N-ethyl-diisopropylamine at 60° C. to yield 4-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile as a white lyophilisate; MS: [M+H]+=402.

Sources & evidence

ORD record
ord-386a10fe3eac4ae18f96f8b8689c1372
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

Loading…