5-Bromo-2-chloropyrimidine
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5-Bromo-2-chloropyrimidine
structure -
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CAS No:
32779-36-5
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Formula:
C4H2N2BrCl
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Chemical Name:
5-Bromo-2-chloropyrimidine
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Synonyms:
2-Chloro-5-Bromopyrimidine;Pyrimidine, 5-bromo-2-chloro-;MAJORIMPURITYIS;2C5BP;
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CAS No:
Characteristics
25.8
1.9
off-white to beige crystalline powder
1.9±0.1 g/cm3
76-81 °C(lit.)
291°C at 760 mmHg
130.1±19.8 °C
1.588
H2O: insoluble
Safety Information
UN 3335
3
R36/37/38
S26-S36/39-S37/39
Xi:Irritant
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 52 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Bromo-2-chloropyrimidine Use and Manufacturing
Phosphorus oxychloride (225 mL, 2.4 mol, 1.4 equiv) was added to a mixture of 5-bromo-2-hydroxypyrimidine (30 g, 0.17 mol) and dimethylaniline (7.5 mL) and the solution heated at reflux under NTo a stirred solution of 5-bromopyrimidin-2-ol (1.0 g, 1.0 eq) in POOl3 (1 mL) dimethylaniline (0.21 g, 0.3 eq) was added under nitrogen atmosphere. Then, thereaction mixture was refluxed at 100 00 for 3 h. After cooling, the reaction mixture was basified with saturated sodium carbonate solution and extracted with ethyl acetate. Organic layer was then separated and dried over Na2SO4 and concentrated to get the crude which was then subjected to the combiflash-12 g silica to isolate the title product as an off white solid (0.67 g, 61.41percent).1H NMR: (DMSO-d6, 300MHz) 69.00-9.01(d, 2H).To a stirred solution of 5-bromopyrimidin-2-ol (1.0 g, 1.0 eq) in P0013 (1 mL) dimethylaniline (0.21 g, 0.3 eq) was added under nitrogen atmosphere. Then, the reaction mixture was refluxed at 1 00 00 for 3 h. After cooling, the reaction mixturewas basified with saturated sodium carbonate solution and extracted with ethyl acetate. The organic layer was then separated and dried over Na2S04 and concentrated to get a crude which was then subjected to the combiflash-12 g silica and isolated the title product as an off white solid (0.67 g, 61 .41 percent).1H NMR: (DMS0- d6, 300MHz) 6 9.00-9.01 (d, 2H).Preparation of 5-Bromo-2-chloro-pyrimidine Synthesis of Compound 11-2 (0399) Compound 11-1 (5.0 g, 2.86 mmol) was added portionwise to POClIn a reaction flask was added 11.5 g (0.1 mol) of 2-chloropyrimidine, bromination reagent NBS 21.3 g (0.12 mol) and acetonitrile 80 mL. A catalytic amount of 2.8 g (0.02 mol) of BF3-Et2O was added at room temperature. After the addition was complete, heating to reflux for 5-8 hours. Completion of the reaction was detected by TLC. Cooling. After insoluble solids were filtered off, after distilling the solvent under reduced pressure, ethyl acetate was added to dissolve followed by dropwise addition of 45 mL of saturated Na2CO3 solution. The organic layer was separated. The aqueous layer was further mixed with 60 mL of ethyl acetate and stratified again. After combining the organic layers, washed with a saturated saline solution. Dried to give 14.1 g of pale yellow 2-chloro-5-bromopyrimidine as a solid. It was used directly in the next reaction.24g 2-chloropyrimidine was added to 200ml acetic acid, 50g bromine was added dropwise, heated to reflux overnight, cooled, Water and ethyl acetate were added, the extracts were separated, the organic phase was collected, dried and concentrated to give 29 g of 5-bromo-2-chloropyrimidine.24 g of 2-chloropyrimidine was added to 200 ml of acetic acid, and 50 g of bromine was added dropwise. The mixture was heated under reflux and stirred overnight. After cooling, water and ethyl acetate were added and the mixture was extracted and collected. The organic phase was collected, dried, and concentrated to give 29 g of 5-bromo-. 2-chloropyrimidine.
5-Bromo-2-chloropyrimidine is a intermediate in the synthesis of pharmaceutical goods such as inhibitors.
Computed Properties
Molecular Weight:193.43
XLogP3:1.9
Hydrogen Bond Acceptor Count:2
Exact Mass:191.90899
Monoisotopic Mass:191.90899
Topological Polar Surface Area:25.8
Heavy Atom Count:8
Complexity:72.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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