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5-Bromo-2-methoxypyrimidine

Product Name5-Bromo-2-methoxypyrimidine
CAS14001-66-2
MFC5H5BrN2O
MW189.01
EINECS626-366-7
MOL File14001-66-2.mol

Chemical Properties

Melting point	55.5-59.5 °C (lit.)
Boiling point	259.8±32.0 °C(Predicted)
Density	1.628±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
pka	-0.22±0.22(Predicted)
form	Solid
color	White to yellow (may have pinkish tinge)
InChI	1S/C5H5BrN2O/c1-9-5-7-2-4(6)3-8-5/h2-3H,1H3
InChIKey	DWVCZDMMGYIULX-UHFFFAOYSA-N
SMILES	COc1ncc(Br)cn1
CAS DataBase Reference	14001-66-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	22-43
Safety Statements	37/39
WGK Germany	3
Hazard Note	Irritant
HS Code	29333990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Skin Sens. 1

Usage And Synthesis

Chemical Properties

White solid

Uses

5-Bromo-2-methoxypyrimidine serves as a precursor in Suzuki coupling reactions with methyl-2-{(1R,4R)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclohexyl}acetate and sodium carbonate to synthesize a kind of phenylcyclohexylacetic acids[3]. The compound reacts with Bu3SnH and V-65 to produce 5-deutero-2-methoxypyrimidine via a deuteration protocol[4].

Synthesis

124-41-4

32779-36-5

14001-66-2

Synthesis of compound 11-3 (5-bromo-2-methoxypyrimidine): to a solution of 5-bromo-2-chloropyrimidine (11-2, 2.0 g, 10 mmol) in methanol (15 mL) was added sodium methanolate (CH3ONa, 2.16 g, 40 mmol). The reaction mixture was stirred at 70 °C overnight. Upon completion of the reaction, methanol was removed by rotary evaporator under reduced pressure. Water (10 mL) was slowly added to the residue, followed by extraction with ethyl acetate (300 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated to give 11-3 as a yellow solid (1.17 g, 60% yield).

References

[1] Patent: US9138427, 2015, B2. Location in patent: Page/Page column 289-290
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5849 - 5853
[3]Fan, J., de Jonge, B. L. M., MacCormack, K., Sriram, S., McLaughlin, R. E., Plant, H., Preston, M., Fleming, P. R., Albert, R., Foulk, M., & Mills, S. D. (2014). A Novel High-Throughput Cell-Based Assay Aimed at Identifying Inhibitors of DNA Metabolism in Bacteria. Antimicrobial Agents and Chemotherapy, 58(12), 7264–7272. https://doi.org/10.1128/aac.03475-14
[4]Mutsumi, T., Iwata, H., Maruhashi, K., Monguchi, Y., & Sajiki, H. (2011). Halogen–deuterium exchange reaction mediated by tributyltin hydride using THF-d8 as the deuterium source. Tetrahedron, 67(6), 1158–1165. https://doi.org/10.1016/j.tet.2010.12.007

5-Bromo-2-methoxypyrimidine

Chemical Properties

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