Potassium tert-butoxide → 2-Chloro-5H-pyrrolo[2,3-B]pyrazine

HRID 386407

Reaction equation

CC(C)([O-])C.[K+].[Cl:7][C:8]1[N:9]=[C:10]([C:15]#[C:16][Si](CC)(CC)CC)[C:11]([NH2:14])=[N:12][CH:13]=1>CN1CCCC1=O.[Cl-].[Na+].O>[Cl:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:16][NH:14][C:11]2=[N:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of potassium tert-butoxide (1 g, 4.5 mM) in N-methylpyrrolidone (3 ml) was heated to 80° C. under nitrogen. A solution of 5-chloro-3-(triethyl-silanylethynyl)-pyrazin-2-ylamine (3) (1.2 g, 4.5 mmol) in N-methylpyrrolidone (10 ml) was added dropwise. The reaction mixture was stirred at 80° C. for a further fifty minutes and then the reaction mixture was allowed to cool to room temperature. Brine (10 ml) was added to the reaction mixture and extracted with ethyl acetate (5×20 ml). The combined organics were washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a solution in N-methylpyrrolidone. MS (ES+): 154

Workup

temperatureto cool to room temperature
extractionextracted with ethyl acetate (5×20 ml)
washThe combined organics were washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d8a8fc7882ee4968b2e53b2d95380ef9
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372835B2

Linked notes

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