Ethane, 2-bromo-1,1-diethoxy- → tert-Butyl 4-(5-bromoimidazo[1,2-a]pyrazin-8-yl)piperazine-1-carboxylate

HRID 1045750Notes

Reaction equation

HRID 1045750 reaction equation
[NH2:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.Br[CH2:23][CH:24](OCC)OCC>CC(O)C>[Br:8][C:6]1[N:7]2[CH:23]=[CH:24][N:1]=[C:2]2[C:3]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 58446968Tert-butyl 4-(3-amino-5-bromopyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 10249304tert-Butyl 4-(5-bromoimidazo[1,2-a]pyrazin-8-yl)piperazine-1-carboxylateYield 23.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 500 mL round bottom flask was charged with tert-butyl 4-(3-amino-5-bromopyrazin-2-yl)piperazine-1-carboxylate (4.0 g, 11.2 mmol), 2-bromo-1,1-diethoxyethane (3.3 g, 16.5 mmol) and absolute propan-2-ol (200 mL). The resulting solution was refluxed under N2 for 12 h. Work-up: the resulting crystalline solid was collected by filtration, washed with EtOAc (100 mL), and dried to afford 1.0 g (23%) of the product as a yellow solid.

Workup

  1. temperatureThe resulting solution was refluxed under N2 for 12 h
  2. filtrationthe resulting crystalline solid was collected by filtration
  3. washwashed with EtOAc (100 mL)
  4. customdried

Sources & evidence

ORD record
ord-48f86dd559bf41038b57ec51e7442427
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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