5-bromo-1H-pyrimidin-4-one Chemical Properties

Melting point:

198-200℃

Density 

2.00±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

7.25±0.40(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C4H3BrN2O/c5-3-1-6-2-7-4(3)8/h1-2H,(H,6,7,8)

InChIKey

CLJIGLPOBRSBNU-UHFFFAOYSA-N

SMILES

C1=NC=C(Br)C(=O)N1

EPA Substance Registry System

5-Bromo-4(1H)-pyrimidinone (19808-30-1)

Safety Information

TSCA 

Yes

HS Code 

2933599590

5-bromo-1H-pyrimidin-4-one Usage And Synthesis

Uses

5-Bromopyrimidine-4-one is a pyrimidine derivative and can be used as a pharmaceutical intermediate.

Synthesis

Step A: Preparation of 5-bromopyrimidin-4(3H)-one: bromine (16.0 mL, 312 mmol) was slowly added dropwise to a suspension of chloroform (1 L) of 4-hydroxypyrimidine (30 g, 312 mmol) at 0 °C. Methanol (10 mL) was then added as a catalyst and the reaction mixture was stirred at 0 °C for 12 hours. Upon completion of the reaction, the resulting white solid product was collected by filtration, washed sequentially with hexane and ether, and then dried under vacuum to afford 5-bromopyrimidin-4-one (50 g, 91.5% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 11.15 (broad single peak, 1H), 8.42 (single peak, 1H), 8.40 (single peak, 1H).

References

[1] Patent: US2007/238726, 2007, A1. Location in patent: Page/Page column 75
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 3905 - 3912
[3] Journal of the Chemical Society, 1955, p. 3478,3481
[4] Patent: WO2013/111105, 2013, A1. Location in patent: Page/Page column 125

5-bromo-1H-pyrimidin-4-one(19808-30-1)Related Product Information

• 5-bromo-1H-pyrimidin-4-one
• 5-BROMO-2,4-DIMETHOXYPYRIMIDINE
• 5-Bromo-4,6-dihydroxypyrimidine
• 2-AMINO-5-BROMO-4-HYDROXY-6-METHYLPYRIMIDINE
• 5-Bromo-4,6-dimethoxypyrimidine
• 5-bromo-2-methylsulfanyl-3H-pyrimidin-4-one
• 2 , 4-BIS(BENZYLOXY)-5-BROMOPYRIMIDINE
• 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE
• 2,4-DI-(TERT-BUTOXY)-5-BROMOPYRIMIDINE
• 5-Bromopyrimidine
• 5-BROMO-2,4-DIAMINO-6-HYDROXYPYRIMIDINE
• 5-bromo-2-phenylpyrimidin-4-ol
• 5-bromo-6-tert-butyl-4-pyrimidinol
• 6-AMINO-5-BROMO-2-(ETHYLTHIO)PYRIMIDIN-4-OL
• 5-bromo-2-(methylsulfanyl)pyrimidin-4-ol
• 5-BROMO-6-METHYLPYRIMIDIN-4-OL
• N-(5-BROMO-1,4-DIHYDRO-4-OXO-6-PHENYL-2-PYRIMIDINYL)-ACETAMIDE
• N-(5-BROMO-4-METHOXY-6-METHYLPYRIMIDIN-2-YL)ACETAMIDE