Diisopropylethylamine → 2,4-Bis-(2-hydroxy-ethylamino)-6-[4-(2-methylsulfanyl-phenyl)-piperazin-1-yl]-pyrimidine-5-carbonitrile

HRID 1838149Notes

Reaction equation

HRID 1838149 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.[CH3:18][S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[OH:17][CH2:16][CH2:15][NH:14][C:4]1[N:5]=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[C:7]([C:8]#[N:9])=[C:2]([N:29]2[CH2:28][CH2:27][N:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19][CH3:18])[CH2:31][CH2:30]2)[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27368951-(2-(Methylthio)phenyl)piperazineHCID 187532174-Chloro-2,6-bis[(2-hydroxyethyl)amino]pyrimidine-5-carbonitrile

Product 1

HCID 187532542,4-Bis-(2-hydroxy-ethylamino)-6-[4-(2-methylsulfanyl-phenyl)-piperazin-1-yl]-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 1-(2-methylsulfanyl-phenyl)-piperazine in dioxane in the presence of N-ethyl-diisopropylamine at 60° C. to yield the 2,4-bis-(2-hydroxy-ethylamino)-6-[4-(2-methylsulfanyl-phenyl)-piperazin-1-yl]-pyrimidine-5-carbonitrile as a yellowish lyophilisate; MS: [M+H]+=430.

Sources & evidence

ORD record
ord-c8ab1df0046146588f33d7ca0ebea656
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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