Chlorine → 1-(2,4-Dichloropyrimidin-5-yl)ethan-1-one
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:11])[CH3:10])=[CH:4][N:3]=1.CC1(C)N([O])C(C)(C)CCC1.C(=O)(O)[O-].[Na+].ClCl>C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](=[O:11])[CH3:10])=[CH:4][N:3]=1Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 0 °C
Procedure
To a stirred suspension of 1-(2,4-dichloro-pyrimidin-5-yl)-ethanol (Example 20, 1.00 g, 5.2 mmol) in a mixture of methylene chloride (30 mL), THF (8 mL) and water (2 mL), tetrabutylammonium chloride (Aldrich, 50 mg, 0.15 mmol), TEMPO (Aldrich, 9 mg, 0.05 mmol) and sodium bicarbonate (208 mg, 2.48 mmol) were added and the mixture was cooled to 0° C. To the stirred mixture, colorex (Aldrich; active Cl2, 10-13%; 3.75 mL) was added and the mixture was stirred for 2 hours at 0° C. Water (10 mL) was added and the organic layer was separated and dried over sodium sulfate. Removal of solvent gave an oil which was purified by silica gel chromatography (1% MeOH/CH2Cl2) to yield a colorless oil. 232 mg, 23%. MS (M+H)+, 191.
Workup
- additionwere added
- customthe organic layer was separated
- dry with materialdried over sodium sulfate
- customRemoval of solvent
- customgave an oil which
- customwas purified by silica gel chromatography (1% MeOH/CH2Cl2)
- customto yield a colorless oil
Sources & evidence
- ORD record
- ord-08afe15dbd4d464195433ac037f25b92
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405220B2
Reaction notes
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