Acetic Anhydride → N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-acetamide
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[CH3:12][C:13](OC(C)=O)=[O:14]>N1C=CC=CC=1>[C:8]([C:7]1[C:2]([NH:1][C:13](=[O:14])[CH3:12])=[N:3][C:4]([S:10][CH3:11])=[N:5][CH:6]=1)#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of 4-amino-2-methylsulfanyl-pyrimidine-5-carbonitrile (5.45 g) in pyridine (66 mL) was added Ac2O (31 mL) at RT. The reaction mixture was stirred at 80° C. for 23 h, then was cooled to RT and evaporated under reduced pressure. The residue was dissolved in DCM (150 mL) and washed with NaHCO3 (sat'd aq) and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (from 0 to >50% EtOAc/Hexane in 20 min.) to give 3.25 g (48% yield) of N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-acetamide as a yellow solid. MS=167 [M−C2H3O+1]+.
Workup
- temperaturewas cooled to RT
- customevaporated under reduced pressure
- dissolutionThe residue was dissolved in DCM (150 mL)
- washwashed with NaHCO3 (sat'd aq) and brine
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified by flash chromatography (from 0 to >50% EtOAc/Hexane in 20 min.)
Sources & evidence
- ORD record
- ord-9667f66378894c3389375654d4b8f8e0
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268840B2
Reaction notes
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