Hydrochloric Acid → 2-{4,6-dichloro-2-[(3S)-3-methylmorpholin-4-yl]pyrimidin-5-yl}ethanol
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:3]=1.C([Li])CCC.[O:21]1[CH2:25][CH2:24]OS1(=O)=O.Cl>C1COCC1>[Cl:8][C:6]1[C:7]([CH2:24][CH2:25][OH:21])=[C:2]([Cl:1])[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:5]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of (3S)-4-(4,6-dichloropyrimidin-2-yl)-3-methylmorpholine (992 mg, 4.0 mmol) in THF (20 mL) was added n-butyllithium (1.56 mL, 1.6 M) dropwise at −78° C. and the mixture was stirred for 30 min. 1,3,2-dioxathiolane 2,2-dioxide (672 mg, 5.41 mmol) was added, and stirring was continued for 30 min, whereupon 6 N HCl (13.3 mL) was added. The reaction mixture was stirred for 18 h and then heated at 40° C. for 4 h. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried with MgSO4, filtered and concentrated by rotary evaporation.
Workup
- stirringstirring
- additionwas added
- stirringThe reaction mixture was stirred for 18 h
- extractionThe reaction mixture was extracted with ethyl acetate
- washthe organic layer was washed with brine
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-fbc680c92f044096a0c00fd097156828
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260439B2
Reaction notes
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