Reaction equation
Cl.[C:2]1([C:8]#[C:9][C:10]2[S:14][C:13]([C:15]3[N:16]=[C:17]4[CH:22]=[N:21][CH:20]=[CH:19][N:18]4C=3N)=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CI.CC(=O)OCC.[CH3:35][N:36]([CH:38]=O)[CH3:37]>>[CH3:35][N:36]([CH3:37])[C:38]1[N:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:17]2=[N:16][C:15]=1[C:13]1[S:14][C:10]([C:9]#[C:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:11][CH:12]=1Participants
Reactant 5
Product 1
Procedure
790 mg (2.5 mmol) of 2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine hydrochloride (Example 83) were dissolved in DMF (8 ml). After addition of 300 mg (7.5 mmol) of sodium hydride (60% dispersion in mineral oil) in portions, the mixture was stirred at RT for 30 min. 0.3 ml (5.0 mmol) of methyl iodide dissolved in DMF (2 ml) was then added dropwise. The reaction solution was stirred at RT for a further 4 h and then quenched with water (20 ml) and extracted with EA (2×50 ml). The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 351 mg (1.0 mmol, 40% of theoretical) of dimethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained from the group by crystallisation (EA).
Workup
- additionwas then added dropwise
- stirringThe reaction solution was stirred at RT for a further 4 h
- customquenched with water (20 ml)
- extractionextracted with EA (2×50 ml)
- dry with materialThe combined organic phases were dried over MgSO4
- filtrationfiltered
- customevaporated under a vacuum
Sources & evidence
- ORD record
- ord-50c0cdb68f814427b1b24cf1ab8a756a
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420056B2
Linked notes
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