Thionyl Chloride → 5-methyl-6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one
Reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([OH:14])=O.S(Cl)(Cl)=O.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:14]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of pure 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, (0.1 g, 0.47 mmol) in DMF (5 mL) was added dropwise thionyl chloride (0.034 mL, 0.47 mmol). The reaction mixture was stirred at 0° C. for 15 min. Pyrrolidine (0.12 mL, 1.4 mmol) was then added and the reaction was allowed to warm to RT over 1 h. The reaction mixture was quenched with saturated NaHCO3 (25 mL) and extracted with EtOAc (25 mL). The organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated to give 0.080 g of pure 5-methyl-6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one, (yield: 65%).
Workup
- temperatureto warm to RT over 1 h
- customThe reaction mixture was quenched with saturated NaHCO3 (25 mL)
- extractionextracted with EtOAc (25 mL)
- washThe organic layer was washed with brine (30 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-90e2ca160ddf45cfbf02abb433fa6603
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08133998B2
Reaction notes
Loading…