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Product Details

Product Name5-Bromo-1-methylpyrimidin-2(1H)-one
CAS No.14248-01-2Molecular Weight189.01
FormulaC5H5BrN2OMDL No.MFCD11044136
Boiling Point- InChI KeyPTRMFRSWZCJCSP-UHFFFAOYSA-N
PubChem ID139707
ClogP
Synonyms

Safety

GHS Pictogram
Signal WordWarningClassN/A
Precautionary StatementsP261-P280-P305+P351+P338UN#N/A
Hazard StatementsH302-H315-H319-H332-H335Packing GroupN/A

Application In Synthesis

Synthesis Path-Downstream   1~4

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YieldReaction ConditionsOperation in experiment
385 mg With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5.00 h; Step 1:
5-Bromo-1-methylpyrimidin-2(1H)-one
A mixture of 5-bromopyrimidin-2(1H)-one (3 g), methyliodide (1.1 mL) and K2CO3 (2.4 g) in N,N-dimethylformamide (60 mL) is stirred for 5 hours at room temperature.
The mixture is filtered and the mother liquor is concentrated.
The residue is partitioned between water and dichloromethane.
The organic phase is washed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 385 mg; LC (method 9): tR=0.25 min; Mass spectrum (ESI+): m/z=189 [M+H]+.
385 mg With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5.00 h; A mixture of 5-bromopyrimidin-2(1 H)-one (3 g), methyliodide (1 .1 ml_) and K2CO3 (2.4 g) in N,N-dimethylformamide (60 mL) is stirred for 5 hours at room temperature. The mixture is filtered and the mother liquor is concentrated. The residue is partitioned between water and dichloromethane. The organic phase is washed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 385 mg; LC (method 9): tR = 0.25 min; Mass spectrum (ESI+): m/z = 189 [M+H]+.
Reference: [1] Patent: US2013/252937, 2013, A1. Location in patent: Paragraph 0767
[2] Patent: WO2013/144097, 2013, A1. Location in patent: Page/Page column 164
[3] Patent: WO2015/160636, 2015, A1. Location in patent: Page/Page column 155
[4] Patent: WO2015/160634, 2015, A1. Location in patent: Page/Page column 142
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YieldReaction ConditionsOperation in experiment
45% With potassium carbonate; dimethyl sulfoxide In water; ethyl acetate 1)
Production of 5-bromo-1-methyl-2(1H)-pyrimidone:
With cooling with ice, potassium carbonate (7.56 g, 54.7 mmol) and methyl iodide (1.27 ml, 20.3 mmol) were added to a dimethyl sulfoxide (100 mL) solution of 5-bromo-2-hydroxypyrimidine hydrobromide (4.0 g, 15.6 mmol), and stirred at 15°C for 16 hours.
Water was added to the reaction mixture, and extracted three times with ethyl acetate.
The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate and then concentrated under reduced pressure.
The residue was suspended in ethyl acetate, then filtered and dried to obtain the entitled compound (1.33 g, 45 percent).
Reference: [1] Patent: WO2006/59778, 2006, A1. Location in patent: Page/Page column 46
[2] Patent: EP1820797, 2007, A1
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Reference: [1] Patent: US4395406, 1983, A

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