Triethylamine → 5-Bromo-2-(methylsulfanyl)-4-[(methylsulfonyl)methyl]pyrimidine
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][S:7][CH:8]1[N:13](C)[C:12](O)=[C:11]([Br:16])[CH:10]=[N:9]1.[CH3:17]CN(CC)CC>C(Cl)Cl>[Br:16][C:11]1[C:10]([CH2:1][S:2]([CH3:17])(=[O:4])=[O:3])=[N:9][C:8]([S:7][CH3:6])=[N:13][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
MsCl (5.85 g, 51.0 mmol) was added to a stirred, cooled 0° C. mixture of 2-methylthio-5-bromo-3-methylhydroxy pyrimidine (10 g, 42.5 mmol) in CH2Cl2 (200 mL), followed by addition of Et3N (6.46 g, 63.8 mmol). The mixture was stirred at 0° C. for 30 min. TLC showed no starting material left. The mixture was quenched with water (30 mL) and the mixture was washed with more water (50 mL). The organic fraction were washed with brine (saturated, 50 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 65i, eluting with EtOAc/hexane (3/7) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 8.61 (s, 1H), 5.38 (s, 2H), 3.21 (s, 3H), 2.60 (s, 3H).
Workup
- waitleft
- customThe mixture was quenched with water (30 mL)
- washthe mixture was washed with more water (50 mL)
- washThe organic fraction were washed with brine (saturated, 50 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel Biotage 65i
- washeluting with EtOAc/hexane (3/7)
Sources & evidence
- ORD record
- ord-8ada14f1100b4b5096d0d33d63a4a4d4
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221834B2
Reaction notes
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