(S)-1-Boc-3-methylpiperazine → (S)-tert-Butyl 4-(5-Bromopyrazin-2-yl)-3-methylpiperazine-1-carboxylate

HRID 1021998Notes

Reaction equation

HRID 1021998 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Br:15][C:16]1[CH:21]=[N:20][C:19](Br)=[CH:18][N:17]=1>>[Br:15][C:16]1[N:17]=[CH:18][C:19]([N:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][C@@H:2]2[CH3:1])=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 7023035(S)-1-Boc-3-methylpiperazineHCID 114704212,5-dibromopyrazine

Product 1

HCID 86684426(S)-tert-Butyl 4-(5-Bromopyrazin-2-yl)-3-methylpiperazine-1-carboxylateYield 19%

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-tert-butyl 3-methylpiperazine-1-carboxylate (6.0 g, 30 mmol) and 2,5-dibromopyrazine (14.1 g, 60 mmol) was stirred at 80° C. for 15 h. It was then cooled to room temperature and purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (10:1 to 2:1) to afford 230a as a yellow solid (1.14 g, 19%). MS: [M+H]+ 359.1.

Workup

  1. temperatureIt was then cooled to room temperature
  2. custompurified by silica-gel column chromatography
  3. washeluting with petroleum ether/ethyl acetate (10:1 to 2:1)

Sources & evidence

ORD record
ord-376f217b40444746bd1840563edf7ecd
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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