3-Amino-9-ethylcarbazole → (2-Chloro-pyrimidin-4-yl)-(9-ethyl-9H-carbazol-3-yl)-amine

HRID 335379

Reaction equation

HRID 335379 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH2:23][CH3:24])[C:15]3[C:20]([C:21]=2[CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[N:14]([CH2:23][CH3:24])[C:15]4[C:20]([C:21]=3[CH:22]=2)=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 89654106(2-Chloro-pyrimidin-4-yl)-(9-ethyl-9H-carbazol-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Briefly, 2,4-dichloropyrimidine (1) was reacted with 3-amino-9-ethylcarbazole (2) by heating in iso-propanol in the presence of N,N-diisopropylethylamine. Separation of the regioisomers provided the pure 4-substituted pyrimidine derivative (3), which was reacted with 4-(3-Aminopropyl)morpholine (4) in sec-butanol under microwave heating in the presence of N,N-diisopropylethylamine to provide EHop-016 (5).

Workup

  1. customSeparation of the regioisomers

Sources & evidence

ORD record
ord-57420fdc378148f6b93f62605633b0d0
Source dataset
uspto-grants-2014_11
Patent number
US08884006B2

Linked notes

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