Bromine → 5-Bromo-3-methyl-2-(methylthio)pyrimidin-4(3H)-one

HRID 1993345

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]=[C:3]1[S:9][CH3:10].[Br:11]Br>C(Cl)(Cl)Cl>[Br:11][C:6]1[C:7](=[O:8])[N:2]([CH3:1])[C:3]([S:9][CH3:10])=[N:4][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-Methyl-2-methylthio-3H-pyrimidin-4-one (Step 2, 3.31 g, 21.2 mmol) was dissolved in CHCl3 (50 mL) and cooled to 0° C. under Ar. Br2 (1.25 mL, 25.4 mmol) was added via syringe, and the reaction was stirred at 0° C. for 35 min, at which time TLC analysis indicated complete consumption of starting material. The reaction was quenched with 40 mL saturated NaHCO3, warmed to RT, and stirred overnight. The reaction was extracted with CH2Cl2 (3×25 mL), and the organic extracts were combined, dried over Na2SO4, filtered, and concentrated to give the title compound, which did not require further purification. MS (ESI pos. ion) m/z: 236. Calc'd for C6H7BrN2OS: 233.95.

Workup

customconsumption of starting material
customThe reaction was quenched with 40 mL saturated NaHCO3
temperaturewarmed to RT
stirringstirred overnight
extractionThe reaction was extracted with CH2Cl2 (3×25 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-282f4e6c7edd441e8a0958f1a23ec8c7
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Linked notes

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