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Triethylamine → N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

HRID 29112
Notes
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Reaction equation

HRID 29112 reaction equation
[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][N:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[CH:21])=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=1.CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CC(=O)OCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)=O.CC#N>[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][N:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[C:21][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=2)=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 792052-Bromo-6-methylpyridineHCID 86613493Tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

Product 1

HCID 69319611N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amineYield 42%

Reagents, catalysts & solvents

5
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21918305Acetone acetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

300 mg (1.0 mmol) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were dissolved together with 138 μl (1.2 mmol) of 2-bromo-6-methyl-pyridine in DMF (7 ml). 1.4 ml (10.0 mmol) of NEt3, 19 mg (0.1 mmol) of copper(I) iodide and 71 mg (0.1 mmol) bis(triphenylphosphine)-palladium(II) chloride were added to this solution. The reaction mixture was heated to 50° C. for 6 h. The mixture was then diluted with EA and combined with a 1M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 166 mg (0.42 mmol, 42%) of N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (acetone/MeCN 1:1) of the group.

Workup

  1. customThe phases were separated
  2. extractionthe aq. phase was extracted with EA
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under a vacuum

Sources & evidence

ORD record
ord-7cde2f995f364bf295165dd97c1841c8
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07420056B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes