Triethylamine → 5-Bromo-2-(methylsulfanyl)-4-[(methylsulfonyl)methyl]pyrimidine

HRID 531226

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[C:8]([CH2:15]O)=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1.CCN(CC)CC>C(Cl)Cl>[Br:6][C:7]1[C:8]([CH2:15][S:2]([CH3:1])(=[O:4])=[O:3])=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonyl chloride (5.85 g, 51.0 mmol) was added to a stirred, cooled 0° C. mixture of [5-bromo-2-(methylthio)pyrimidin-4-yl]methanol (INTERMEDIATE 1, 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 minutes. 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 portion was washed with brine (saturated, 50 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography, 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 portion was 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
washeluting with EtOAc/hexane (3/7)

Sources & evidence

ORD record: ord-9523fc0df1404210b9ebefe97b8a30bf
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353101B2

Linked notes

Loading…