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Methyl iodide → N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

HRID 29109
Notes
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Reaction equation

HRID 29109 reaction equation
[H-].[Na+].[C:3]([NH:7][C:8]1[N:12]2[CH:13]=[CH:14][N:15]=[CH:16][C:11]2=[N:10][C:9]=1[C:17]1[S:18][C:19]([C:22]#[C:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:20][CH:21]=1)([CH3:6])([CH3:5])[CH3:4].CI.[C:32]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CC(C)=O.CC#N.CC(=O)OCC.C1COCC1.O>[C:3]([N:7]([CH3:32])[C:8]1[N:12]2[CH:13]=[CH:14][N:15]=[CH:16][C:11]2=[N:10][C:9]=1[C:17]1[S:18][C:19]([C:22]#[C:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:20][CH:21]=1)([CH3:6])([CH3:4])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6328Methyl iodide2×HCID 10340Sodium CarbonateHCID 24758Sodium hydride2×HCID 69320139Tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

Product 1

HCID 11509312N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amineYield 24%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 21918305Acetone acetonitrileSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

43 mg (1.08 mmol, 60% in mineral oil) of sodium hydride were added to a solution of 135 mg (0.36 mmol) of tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (Example 77) in DMF (3 ml) and the mixture was stirred at RT for 1 h. A solution of 67 μl (1.08 mmol) of methyl iodide in DMF (500 μl) was then added dropwise thereto and the mixture stirred at RT for a further 16 h. A further 43 mg (1.08 mmol, 60% in mineral oil) of sodium hydride and a solution of 67 μl (1.08 mmol) of methyl iodide in DMF (500 μl) were then added and the mixture stirred at RT for a further 16 h. The reaction solution was combined in succession with water, a 1M aq. Na2CO3 solution and a mixture of EA/THF (3:1). The organic phase was separated off and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 33 mg (0.09 mmol, 24%) of N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (acetone/MeCN 1:1).

Workup

  1. stirringthe mixture stirred at RT for a further 16 h
  2. stirringthe mixture stirred at RT for a further 16 h
  3. customThe organic phase was separated off
  4. extractionthe aq. phase was extracted with EA
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under a vacuum

Sources & evidence

ORD record
ord-bf47b26a471942c28ecd580368cf78b2
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07420056B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes