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

Base Information

• Chemical Name: 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE
• CAS No.: 56741-95-8
• Molecular Formula: C10H8BrN3O
• Molecular Weight: 266.097
• Hs Code.: 2933599090
• Mol file: 56741-95-8.mol

Synonyms:Bropirimine;2-Amino-5-bromo-6-phenyl-1H-pyrimidin-4-one;4-Pyrimidinol, 2-amino-5-bromo-6-phenyl-;4 (1H)-Pyrimidinone, 2-amino-5-bromo-6-phenyl-;2-Amino-5-bromo-6-phenyl-4(1H)-pyrimidinone;ABPP;4(1H)-Pyrimidinone, 5-bromo-2, 3-dihydro-2-imino-6-phenyl-;4(1H)-Pyrimidinone,2-amino-5-bromo-6- phenyl-;U-54461;

Chemical Property of 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE

Chemical Property:

• Vapor Pressure: 2.8E-06mmHg at 25°C
• Melting Point: 285-287° (Stevens); mp 246-248° (Brown, Stevens)
• Refractive Index: 1.715
• Boiling Point: 389.7 °C at 760 mmHg
• PKA: 3.18; 8.53(at 25℃)
• Flash Point: 189.5 °C
• PSA: 72.03000
• Density: 1.74 g/cm³
• LogP: 2.77510
• Storage Temp.: room temp
• Solubility.: DMSO: ≥5mg/mL (warm DMSO)
• Water Solubility.: 7.8mg/L(37 oC)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bropirimine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63-62

MSDS Files:

SDS file from LookChem

Useful:

• 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. 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.

Technology Process of 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE

There total 9 articles about 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

C10H7BBrF3N3(1-)*K(1+) → bropirimine (56741-95-8)

Guidance literature:

With dihydrogen peroxide; sodium carbonate; In ethanol; at 55 ℃; for 24h;

DOI:10.1002/anie.202101297

Reference yield: 60.0%

2-amino-6-phenyl-3H-pyrimidin-4-one (56741-94-7) → bropirimine (56741-95-8)

Guidance literature:

With bromine; acetic acid; at 20 - 70 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2015.04.084

Reference yield:

ethyl 3-oxo-3-phenylpropionate (94-02-0) → bropirimine (56741-95-8)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol; toluene / Heating

2: bromine / acetic acid / 3 h / Ambient temperature

With bromine; In ethanol; acetic acid; toluene;

DOI:10.1021/jm00150a018

upstream raw materials:

2-amino-6-phenyl-3H-pyrimidin-4-one

ethyl 3-oxo-3-phenylpropionate

benzoyl chloride

methyl 3-oxo-3-phenylpropionate

Downstream raw materials:

5-bromo-2-ethoxycarbonylamino-6-phenyl-4(3H)-pyrimidinone

2-amino-5,6-diphenylpyrimidin-4(3H)-one

7-bromo-1-ethoxycarbonylmethyl-4,6-dioxo-8-phenyl-2,3,4,6-tetrahydro-1H-pyrimido<1,2-a>pyrimidine

2-amino-4-methoxy-5-(4-methoxyphenyl)-6-phenylpyrimidine

Refernces

• 1、 Patel, Alpa,Lewis, William,Searle, Mark S.,Stevens, Malcolm F.G.,Moody, Christopher J.. "Synthesis of 6-arylisocytosines and their potential for hydrogen bonding interactions". supporting information. p. 7339 - 7343. Retrieved 2015/08/24.
• 2、 Skulnick,Weed,Eidson,Renis,Wierenga,Stringfellow. "Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents". . p. 1864 - 1869. Retrieved 2007/10/02.