Diisopropylethylamine → 2-Amino-4-[4-(4-fluoro-phenyl)-piperidin-1-yl]-6-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1838204Notes

Reaction equation

HRID 1838204 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Br)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.Cl.[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([N:24]2[CH2:25][CH2:26][CH:21]([C:18]3[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=3)[CH2:22][CH2:23]2)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrileHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochloride

Product 1

HCID 187532532-Amino-4-[4-(4-fluoro-phenyl)-piperidin-1-yl]-6-methylsulfanyl-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to the procedure described in example 20b, the 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile (see example 69) was treated with the 4-(4-fluorophenyl)-piperidine hydrochloride in dioxane in the presence of N-ethyl-diiso-propylamine at room temperature during 36 hours to yield 2-amino-4-[4-(4-fluoro-phenyl)-piperidin-1-yl]-6-methylsulfanyl-pyrimidine-5-carbonitrile as a yellow solid; MS: [M+H]+=344.

Sources & evidence

ORD record
ord-5b23574fe19f4d9aa9963a426cae49b6
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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