Sodium methanethiolate → (5-Methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14]Br)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][S-:18].[Na+]>CC(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14][S:18][CH3:17])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of (5-bromomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (prepared according to WO 02/070494, 1.03 g, 3.575 mmol) in acetone (11.6 mL) was treated with sodium thiomethoxide (0.33 g, 4.473 mmol). The reaction mixture was stirred at 25° C. for 5 h 15 min. The reaction was then concentrated in vacuo, and the residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The aqueous layer was back-extracted with ethyl acetate (100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 5% ethyl acetate/methylene chloride) afforded (5-methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester as a crude white solid (0.45 g, 49%) which was used without further purification.
Workup
- concentrationThe reaction was then concentrated in vacuo
- customthe residue was partitioned between ethyl acetate (200 mL) and water (200 mL)
- extractionThe aqueous layer was back-extracted with ethyl acetate (100 mL)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-88bd57ef58ec4f9ba95c336acb1792e7
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07132425B2
Reaction notes
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