4-Pyrimidinol, 2,6-diamino- (9CI)

Base Information

• Chemical Name: 4-Pyrimidinol, 2,6-diamino- (9CI)
• CAS No.: 100643-27-4
• Molecular Formula: C₄H₆N₄O
• Molecular Weight: 126.118
• Mol file: 100643-27-4.mol

Synonyms:2-[(benzyloxy)methyl]oxirane;2,6-Diamino-4-hydroxyPyrimidine;2,6-Diaminopyrimidin-4-ol;4-PYRIMIDINOL,2,6-DIAMINO-;

Chemical Property of 4-Pyrimidinol, 2,6-diamino- (9CI)

Chemical Property:

• Boiling Point: 288.5 °C at 760 mmHg
• PKA: 10.85±0.10(Predicted)
• Flash Point: 128.3 °C
• PSA: 97.79000
• Density: 1.84 g/cm³
• LogP: 0.09670
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature

Purity/Quality:

97% ^*data from raw suppliers

2,6-Diaminopyrimidin-4-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Pyrimidinol, 2,6-diamino- (9CI)

There total 7 articles about 4-Pyrimidinol, 2,6-diamino- (9CI) 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: 83.0%

guanidine hydrochloride (50-01-1) + ethyl 2-cyanoacetate (105-56-6) → 2,6-diamino-3H-pyrimidin-4-one (100643-27-4,143504-99-8)

Guidance literature:

With methanol; sodium; for 4h; Reflux;

DOI:10.1002/jhet.2586

Reference yield:

sodium methylate (124-41-4) + guanidine nitrate (506-93-4) + methyl 2-cyanoacetate (105-34-0) → 2,6-diamino-3H-pyrimidin-4-one (100643-27-4,143504-99-8)

Guidance literature:

sodium methylate; guanidine nitrate; In methanol; for 1.5h; Inert atmosphere; Reflux;

methyl 2-cyanoacetate; In methanol; for 4h; Time; Reflux;

Reference yield:

cyanoacetyl-guanidine (55034-35-0) → 2,6-diamino-3H-pyrimidin-4-one (100643-27-4,143504-99-8)

Guidance literature:

at 200 ℃;

upstream raw materials:

cyanoacetyl-guanidine

sodium cyanoacetic acid ethyl ester

guanidine nitrate

ethyl 2-cyanoacetate

Downstream raw materials:

2-amino-6-methyl-7-phenyl-3H-pyrido[2,3-d]pyrimidin-4-one

2-amino-6-nitro-3H-pyrido[2,3-d]pyrimidin-4-one

2,5-diaminothiazolo<4,5-d>pyrimidin-7(6H)-one

2-amino-7-phenyl-3H-pyrido[2,3-d]pyrimidin-4-one

Refernces

Spirooxindoles: reaction of 2,6-diaminopyrimidin-4(3H)-one and isatins

10.1016/j.tet.2009.01.013

The research presents a straightforward and efficient method for synthesizing spiro[pyrimido[4,5-b]quinoline-5,5-pyrrolo[2,3-d]pyrimidine] and spiro[indoline-pyrido[2,3-d:6,5-d]dipyrimidine] derivatives through a cyclocondensation reaction of 2,6-diaminopyrimidin-4(3H)-one and isatins in refluxing ethanol. The reaction utilizes a catalytic amount of p-toluene sulfonic acid (p-TSA) as a catalyst and yields the desired spirocyclic compounds in high percentages (ranging from 78% to 90%). The synthesized compounds are characterized using infrared (IR) spectroscopy, proton (1H) and carbon (13C) nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and elemental analysis, which confirm their structures and purity. The study also explores the reaction with N-alkylisatins, leading to the formation of different products, and proposes plausible mechanisms for the observed reactions.

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