Piperazine → 7-bromo-2-chloro-4-(piperazin-1-yl)-5H-pyrimido[5,4-b]indole

HRID 1182844Notes

Reaction equation

HRID 1182844 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([Cl:15])[N:12]=[C:11](Cl)[C:7]=3[NH:8][C:9]=2[CH:10]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([Cl:15])[N:12]=[C:11]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 581184877-bromo-2,4-dichloro-5H-pyrimido[5,4-b]indole

Product 1

HCID 581185447-bromo-2-chloro-4-(piperazin-1-yl)-5H-pyrimido[5,4-b]indoleYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.3 g (4.10 mmol) 7-bromo-2,4-dichloro-5H-pyrimido[5,4-b]indole (Example 4) and 1.3 g (14.8 mmol) piperazine were heated in 50 ml toluene at 65° C. for 3 h. Then, the solvent was removed and the residue was suspended in water and sucked off. 1.3 g (87%) 7-bromo-2-chloro-4-(piperazin-1-yl)-5H-pyrimido[5,4-b]indole was obtained. ESI-MS [m/z]: 366, 368 [M+H]+

Workup

  1. customThen, the solvent was removed

Sources & evidence

ORD record
ord-54d8d0742a374a33b21a6e256fe094b4
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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