Tert-Butyl isocyanide → [2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine

HRID 29096

Reaction equation

HRID 29096 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[C:8]([N+:12]#[C-:13])([CH3:11])([CH3:10])[CH3:9].[Br:14][C:15]1[S:19][C:18]([CH:20]=O)=[CH:17][CH:16]=1.Cl(O)(=O)(=O)=O>C(Cl)Cl>[Br:14][C:15]1[S:19][C:18]([C:20]2[N:1]=[C:2]3[CH:7]=[N:6][CH:5]=[CH:4][N:3]3[C:13]=2[NH:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 23577Tert-Butyl isocyanideHCID 24247Perchloric AcidHCID 784285-Bromothiophene-2-carbaldehydeHCID 78747Aminopyrazine

Product 1

HCID 69317100[2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amineYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

237 mg (2.50 mmol) of 2-aminopyrazine were dissolved together with 208 mg (2.50 mmol) of tert-butylisonitrile and 0.27 ml (2.50 mmol) of 5-bromothiophene-2-carbaldehyde in DCM (5 ml). After addition of perchloric acid (0.25 ml), the mixture was stirred at RT for 5 d. Washing was then performed with a sat. aq. sodium carbonate solution and a sat. aq. common salt solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under a vacuum. After carrying out column chromatography (EA/DIPE/DCM 2:2:1) with the group, 471 mg (1.3 mmol, 54% of theoretical) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine were obtained.

Workup

  1. washWashing
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under a vacuum

Sources & evidence

ORD record
ord-349aa6a045c34d0c965d1e3ca68e6ff0
Source dataset
uspto-grants-2008_09
Patent number
US07420056B2

Linked notes

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