[ CAS No. 14248-01-2 ]

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2D
Chemical Structure| 14248-01-2
Chemical Structure| 14248-01-2
Structure of 14248-01-2

Quality Control of [ 14248-01-2 ]

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Product Details of [ 14248-01-2 ]

CAS No. :14248-01-2MDL No. :MFCD11044136
Formula :C5H5BrN2OBoiling Point :-
Linear Structure Formula :-InChI Key :-
M.W :189.01Pubchem ID :139707
Synonyms :

Computed Properties of [ 14248-01-2 ]

TPSA : 32.7 H-Bond Acceptor Count : 1
XLogP3 : 0.4 H-Bond Donor Count : 0
SP3 : 0.20 Rotatable Bond Count : 0

Safety of [ 14248-01-2 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14248-01-2 ]

  • Upstream synthesis route of [ 14248-01-2 ]
  • Downstream synthetic route of [ 14248-01-2 ]

[ 14248-01-2 ] Synthesis Path-Upstream   1~3

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  • [ 74-88-4 ]
  • [ 14248-01-2 ]
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
  • 3
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Reference: [1] Patent: US4395406, 1983, A
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