4-Hydroxypyrimidine

Base Information

• Chemical Name: 4-Hydroxypyrimidine
• CAS No.: 4562-27-0
• Deprecated CAS: 176773-03-8,542-27-8,542-27-8
• Molecular Formula: C4H4N2O
• Molecular Weight: 96.0886
• Hs Code.: 29335990
• European Community (EC) Number: 257-545-4,224-932-4
• NSC Number: 157911,1575
• UNII: K43V90OY4L
• DSSTox Substance ID: DTXSID5063524
• Nikkaji Number: J90.464C
• Wikidata: Q17572767
• Mol file: 4562-27-0.mol

Synonyms:4-hydroxypyrimidine;4-OH-P

Chemical Property of 4-Hydroxypyrimidine

Chemical Property:

• Appearance/Colour: white-like to grey powdery solid
• Vapor Pressure: 0.725mmHg at 25°C
• Melting Point: 163-167 °C
• Refractive Index: 1.596
• Boiling Point: 184.65 °C at 760 mmHg
• PKA: 9.02±0.40(Predicted)
• Flash Point: 65.475 °C
• PSA: 46.01000
• Density: 1.288 g/cm³
• LogP: 0.18220
• Storage Temp.: 2-8°C
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 96.032362755
• Heavy Atom Count: 7
• Complexity: 137

Purity/Quality:

97% ^*data from raw suppliers

4(3H)-Pyrimidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-40
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrimidines
• Canonical SMILES: C1=CN=CNC1=O

Technology Process of 4-Hydroxypyrimidine

There total 3 articles about 4-Hydroxypyrimidine 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:

Pyrimidin-4-ol (51953-17-4) → 4-pyrimidinone (4562-27-0)

Guidance literature:

at 38 ℃; Equilibrium constant;

DOI:10.1016/0022-2860(94)87026-8

Reference yield:

→ 4-pyrimidinone (4562-27-0)

Guidance literature:

Reference yield:

→ 2-allylamino-1-<(4-fluorophenyl)methyl>pyrido<2,3-d>pyrimidine-4(1H)-one (58536-96-2) + 4-pyrimidinone (4562-27-0)

Guidance literature:

upstream raw materials:

Pyrimidin-4-ol

Downstream raw materials:

pyrimidine-4(3H)-one

Pyrimidin-4-ol

uracil

3-phenyl-5,7a-dihydroisoxazolo[5,4-d]pyrimidin-4(3aH)-one

Refernces

Discovery of IWP-051, a Novel Orally Bioavailable sGC Stimulator with Once-Daily Dosing Potential in Humans

10.1021/acsmedchemlett.5b00479

The study focuses on the development of IWP-051, a potent and orally bioavailable stimulator of soluble guanylate cyclase (sGC). sGC is an enzyme that plays a crucial role in various physiological processes, such as smooth muscle relaxation and vasodilation, via the NO-sGC-cGMP signaling pathway. Impairment of this pathway is linked to cardiovascular and other diseases. The researchers designed and synthesized a series of 4-hydroxypyrimidine sGC stimulators, starting with an internally discovered lead compound. Through structural modifications, they identified IWP-051, which demonstrated good potency, stability, selectivity, and pharmacodynamic effects, along with favorable pharmacokinetic properties suitable for once-daily dosing. Key chemicals involved include the lead compound 1, which showed off-target activity and a short half-life, and various analogs such as 5, 11, and others, which were synthesized to improve potency and pharmacokinetic profiles. IWP-051 exhibited minimal off-target liabilities, high protein binding, low clearance, and a long half-life across species, making it a promising candidate for sustained sGC stimulation in preclinical disease models.