ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyrimidines Bromopyrimidine 6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE

6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE

Product Name6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE
CAS2240-25-7
MFC4H4BrN3O
MW190
EINECS218-806-8
MOL File2240-25-7.mol

Chemical Properties

Melting point	240-243 °C (dec.) (lit.)
Density	1.7513 (rough estimate)
refractive index	1.6520 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Soluble in formic acid (50 mg/ml).
form	Solid
pka	7.34±0.10(Predicted)
color	White to yellow
BRN	127286
InChI	InChI=1S/C4H4BrN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
InChIKey	QFVKLKDEXOWFSL-UHFFFAOYSA-N
SMILES	C1(=O)NC(N)=C(Br)C=N1
NIST Chemistry Reference	5-Bromocytosine(2240-25-7)

Safety Information

Hazard Codes	Xn
Risk Statements	22-37/38-41-43-48-20/21/22
Safety Statements	24/25-22-36/37/39-26-45-7/8
WGK Germany	3
F	10-23
HS Code	29335990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 Skin Sens. 1 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

LIGHT YELLOW AMORPHOUS POWDER

Uses

5-Bromocytosine was used in the synthesis of five cross-link products- C[5-N6]A, C[5-2]A, C[5-8]A, A[2-5]C, and A[8-5]C, under both aerobic and anaerobic conditions.

Uses

4-Amino-5-bromo-2-hydroxypyrimidine can be used in the synthesis of cross-link products under anaerobic and aerobic conditions.

General Description

5-Bromocytosine derivative (β isomer) is a potent anti-HIV agent.

Synthesis

71-30-7

2240-25-7

General procedure for the synthesis of 4-amino-5-bromopyrimidin-2(1H)-one from 6-aminopyrimidin-2(1H)-one: 6-aminopyrimidin-2(1H)-one (55.6 g, 0.5 mol), N-bromosuccinimide (106.8 g, 0.6 mol) and DMF (150 mL) were added to a reaction flask, cooled to 15°C, and ultrasonicated for reaction under ultrasonic condition for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete reaction of the raw materials, it was filtered. The filter cake was washed with distilled water (20 mL×2) and dried to obtain 4-amino-5-bromopyrimidin-2(1H)-one (90.9 g, 95.6% yield).

Purification Methods

5-Bromocytosine is recrystallised from H2O or 50% aqueous EtOH. Alternatively, dissolve ca 3g in conc HCl (10mL) and evaporate to dryness. Dissolve the residual hydrochloride in the minimum volume of warm H2O and make faintly alkaline with aqueous NH3. Collect the crystals and dry them in a vacuum at 100o. [Hilbdert & Jensen J Am Chem Soc 56 134 1934, Beilstein 25 III/IV 3689.]

References

[1] Patent: CN103819412, 2016, B. Location in patent: Paragraph 0023-0025; 0031-0032; 0037; 0038
[2] Synthesis, 2005, # 7, p. 1103 - 1108
[3] Tetrahedron Letters, 1992, vol. 33, # 50, p. 7779 - 7782
[4] Chemistry Letters, 1987, p. 2311 - 2312
[5] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 11, p. 3750 - 3751

6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE manufacturers

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