2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE Chemical Properties

Melting point:

285-287° (Stevens); mp 246-248° (Brown, Stevens)

Boiling point:

389.7±52.0 °C(Predicted)

Density 

1.6292 (rough estimate)

refractive index 

1.6520 (estimate)

storage temp. 

room temp

solubility 

DMSO: ≥5mg/mL (warm DMSO)

form 

powder

pka

3.18; 8.53(at 25℃)

color 

white to beige

Water Solubility 

7.8mg/L(37 ºC)

Safety Information

Hazard Codes 

Xn

Risk Statements 

63-62

WGK Germany 

3

RTECS 

UW7351300

2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE Usage And Synthesis

Description

Bropirimine is an immunomodulator with diverse biological activities. It is a toll-like receptor 7 (TLR7) agonist that inhibits RANKL-induced osteoclast differentiation of murine bone marrow-derived macrophages (BMDMs) in a concentration-dependent manner, an effect that is reversed by an anti-IFN-β antibody. Dietary administration of bropirimine (200 mg/kg twice per week) prevents development of transitional cell carcinomas (TCCs) in a mouse model of carcinogen-induced bladder carcinoma. Bropirimine (100 mg/kg) reduces pulmonary collagen accumulation and bronchoalveolar lavage fluid (BALF) monocyte and eosinophil infiltration in a hamster model of bleomycin-induced lung fibrosis. It also delays disease onset and progression and increases plasma IFN levels in a mouse model of experimental autoimmune encephalomyelitis (EAE).

Uses

Bropirimine is an orally active immunostimulant; anticancer agent. Bropirimine is an interferon inducer that is a potentially useful in the the treatment of superficial bladder cancer (transitional cell carcinoma). Studies suggest that Bropirimine has direct antitumor activity rather than a cytokine-mediated antitumor effect.

Uses

Bropirimine, an immunostimulating agent and toll like receptor (TLR7) agonist, is used in comparison with other TLR7 agonists such as imiquimod, R-848, loxoribine in interferon cell signaling research. Bropirimine may be used in experimental autoimmune encephalomyelitis (EAE) and bladder cancer research.

Definition

ChEBI: Bropirimine is a member of pyrimidines.

Biochem/physiol Actions

Bropirimine is an immunostimulating agent. The compound induces production of α and β interferons and enhances NK cell function. Bropirimine has antiproliferative effects in cancer cell lines and tumor growth in in vivo models.

Synthesis

General procedure for the synthesis of 2-amino-5-bromo-4-hydroxy-6-phenylpyrimidines from 2-amino-4-hydroxy-6-phenylpyrimidines: to a suspension of 2-amino-6-phenylpyrimidin-4(3H)-one (200 mg, 1.07 mmol) in glacial acetic acid (2 mL) was added slowly and dropwise at 70 °C with bromine (57.0 μL, 1.12 mmol) in a glacial acetic acid (2 mL) solution. The reaction mixture was cooled to room temperature and stirring was continued for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was ground with ether (10 mL) and recrystallized from ethanol to give 2-amino-5-bromo-4-hydroxy-6-phenylpyrimidine as a colorless solid (171 mg, 60% yield). The melting point of the product was 275-277 °C (literature value: 285-287 °C); high resolution mass spectrometry (HRMS) measured value: M+H+, 264.9847 (C10H9 79BrN3O+, calculated value 264.9845); infrared spectra (νmax, CHCl3, cm-1): 3691, 3607, 3012, 1692, 1602 , 1473, 1440, 1328, 1240; NMR hydrogen spectrum (1H NMR, 400 MHz, DMSO-d6): δ 7.56-7.53 (2H, m, ArH), 7.45-7.43 (3H, m, ArH), 6.87 (2H, br s, NH2); NMR carbon spectrum (13C NMR, 100 MHz. DMSO-d6): δ 158.6 (C), 153.2 (2×C), 136.3 (C), 129.7 (CH), 128.5 (CH), 128.0 (CH), 97.3 (C); mass spectrum (ESI): m/z 264/266 (M+H+, 34/35%). The spectral data of the obtained product are in agreement with literature reports.

storage

Desiccate at RT

Toxics Screening Level

The initial threshold screening level (ITSL) for bropirimine is 15 μg/m3 based on an annual averaging time.

References

[1] Tetrahedron, 2015, vol. 71, # 39, p. 7339 - 7343
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 5, p. 1315 - 1321
[3] Journal of Medicinal Chemistry, 1980, vol. 23, # 3, p. 237 - 239
[4] Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1864 - 1869

2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE(56741-95-8)Related Product Information

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