Sodium Bicarbonate → (6-Bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanone
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:10]2[C:11]([Cl:17])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=2)[OH:9])[CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl.[Na+]>ClCCl.O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[Br:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[C:11]([Cl:17])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of crude (6-bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanol (from Example 28 supra) (16.1 g, crude) in dichloromethane (200 mL), water (20 mL) was added followed by NaHCO3 (2.1 g, 25 mmol), TBAB (485 mg, 1.5 mmol) and TEMPO (90 mg, 0.5 mmol). The mixture was then cooled to 0° C. and NaClO (70 mL, active chloride >6.0%) was added slowly and the resulting mixture was stirred for 30 minutes. The mixture was poured into water and extracted with dichloromethane. The organic phase was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, eluting with ethyl acetate:petroleum ether, 1:20) to give (6-bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanone as a white solid. (Yield 12.7 g, 76% over two steps).
Workup
- extractionextracted with dichloromethane
- dry with materialThe organic phase was dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography (silica gel, eluting with ethyl acetate:petroleum ether, 1:20)
Sources & evidence
- ORD record
- ord-25de5dddf1f9471b9331a7acf7b73c12
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362023B2
Reaction notes
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