1-(4-Fluorophenyl)piperazine → 2-(Cyclopropylmethyl-amino)-4-[4-(4-fluoro-phenyl)-piperazin-1-yl]-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile

HRID 1838180Notes

Reaction equation

HRID 1838180 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][CH:16]2[CH2:18][CH2:17]2)[N:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[CH:16]1([CH2:15][NH:14][C:4]2[N:3]=[C:2]([N:29]3[CH2:28][CH2:27][N:26]([C:23]4[CH:22]=[CH:21][C:20]([F:19])=[CH:25][CH:24]=4)[CH2:31][CH2:30]3)[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[N:5]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 752601-(4-Fluorophenyl)piperazineHCID 81531DiisopropylethylamineHCID 187532604-Chloro-2-(cyclopropylmethyl-amino)-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile

Product 1

HCID 102730362-(Cyclopropylmethyl-amino)-4-[4-(4-fluoro-phenyl)-piperazin-1-yl]-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to the procedure described in example 47b, 4-chloro-2-(cyclopropylmethyl-amino)-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile (example 48a) was treated with the 1-(4-fluorophenyl)-piperazine in dioxane in the presence of N-ethyl-diisopropyl-amine at 100° C. to yield 2-(cyclopropylmethyl-amino)-4-[4-(4-fluoro-phenyl)-piperazin-1-yl]-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile as an amorphous, white solid; MS: [M+H]+=412.

Sources & evidence

ORD record
ord-56b5b06b71b54eb7b70c6847ba6810fe
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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