4,6-Dihydroxypyrimidine

Base Information

• Chemical Name: 4,6-Dihydroxypyrimidine
• CAS No.: 1193-24-4
• Deprecated CAS: 18337-68-3
• Molecular Formula: C4H4N2O2
• Molecular Weight: 112.088
• Hs Code.: 2933.59
• European Community (EC) Number: 214-772-3
• NSC Number: 22838
• UNII: 6L93V0S662
• DSSTox Substance ID: DTXSID6025434
• Nikkaji Number: J41.160D,J2.426.754G
• Wikidata: Q27265097
• ChEMBL ID: CHEMBL1722176
• Mol file: 1193-24-4.mol

Synonyms:4,6-DIHYDROXYPYRIMIDINE;1193-24-4;pyrimidine-4,6-diol;4,6-Pyrimidinediol;4(1H)-Pyrimidinone, 6-hydroxy-;6-Hydroxy-4(1H)-pyrimidinone;4-hydroxy-1H-pyrimidin-6-one;6-hydroxypyrimidin-4(3H)-one;4(3H)-Pyrimidinone, 6-hydroxy-;6-Hydroxy-4-pyrimidinone;MFCD00016733;4,6-Dihydroxypyrimidin;6-Hydroxy-1H-pyrimidin-4-one;NSC 22838;4,6-Dihydroxypyrimidin [German];EINECS 214-772-3;UNII-6L93V0S662;NSC-22838;6L93V0S662;EC 214-772-3;NSC22838;4,6-dihydroxy pyrimidine;6-hydroxy-4(3h)-pyrimidone;MLS000774924;SCHEMBL152294;6-hydroxy-3H-pyrimidin-4-one;SCHEMBL8088423;4,6-Dihydroxypyrimidine, 98%;CHEMBL1722176;DTXSID6025434;DUFGYCAXVIUXIP-UHFFFAOYSA-;CHEBI:184008;HMS2744P17;BCP00979;STR03284;PYRIMIDINE, 4,6-DIHYDROXY-;LS-624;STL135950;STL139315;AKOS003237466;AKOS005746727;6-hydroxy-3,4-dihydropyrimidin-4-one;AC-2511;CS-W016618;PS-3433;SB57283;4(1H)-PYRIMIDINONE, 6-HYDROXY;NCGC00246132-01;HYDROXY-4(1H)-PYRIMIDINONE, 6-;SMR000368133;SY001718;4,6-Dioxohexahydropyrimidine-2-ylium-5-ide;AM20080136;BB 0242395;D1821;FT-0617255;EN300-25578;AB-323/25048196;W-108518;Q27265097;Z56766633;F0176-0211

Chemical Property of 4,6-Dihydroxypyrimidine

Chemical Property:

• Appearance/Colour: pale yellow crystals
• Vapor Pressure: 0.001Pa at 20℃
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.4610 (estimate)
• Boiling Point: 358.5 °C at 760 mmHg
• PKA: 5.70±0.10(Predicted)
• Flash Point: 170.6 °C
• PSA: 66.24000
• Density: 1.4421 (rough estimate)
• LogP: -0.11220
• Storage Temp.: Store below +30°C.
• Solubility.: 2.5 g/L (20° C)
• Water Solubility.: 2.5 g/L (20 º C)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 112.027277375
• Heavy Atom Count: 8
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

4,6-Dihydroxypyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrimidines
• Canonical SMILES: C1=C(N=CNC1=O)O
• Uses: 4,6-Dihydroxypyrimidine (cas# 1193-24-4) is a compound useful in organic synthesis.

Technology Process of 4,6-Dihydroxypyrimidine

There total 13 articles about 4,6-Dihydroxypyrimidine 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: 99.8%

4,6-dihydroxypyrimidine sodium salt → 4,6-pyrimidinediol (1193-24-4)

Guidance literature:

With hydrogenchloride; Large scale;

Reference yield: 96.0%

malonic acid dimethyl ester (108-59-8) → 4,6-pyrimidinediol (1193-24-4)

Guidance literature:

With sulfuric acid; sodium methylate; formamide; In methanol; water;

Reference yield: 90.0%

formamide (77287-34-4,77287-35-5,60100-09-6) + malonic acid dimethyl ester (108-59-8) → 4,6-pyrimidinediol (1193-24-4)

Guidance literature:

With sodium methylate; In methanol; at 60 - 70 ℃; for 8h; Large scale;

upstream raw materials:

sodium ethanolate

diethyl malonate

formamidine

azoxystrobin

Downstream raw materials:

4,6-dihydroxy-5-benzylthiopyrimidine

5-phenylfuro<2,3-d>pyrimidin-4(3H)-one

5,6-dihydro-6-nitro-5-phenylfuro<2,3-d>pyrimidin-4(3H)one

5-(4-chlorophenyl)furo[2,3-d]pyrimidin-4(3H)-one

Refernces

A convenient synthesis of 4,6-dichloro-5-benzylthiopyrimidine

10.1080/00397919308011121

The study presents a practical and convenient two-step synthesis of the title compound, 4,6-dichloro-5-benzylthiopyrimidine (3), starting from 4,6-dihydroxypyrimidine (1). The initial three-step approach involved converting 4,6-dihydroxypyrimidine (1) to 4,6-dihydroxy-5-bromopyrimidine (4) with an 80% yield. Then, compound (4) was reacted with benzylmercaptan and anhydrous potassium carbonate in N,N-dimethylformamide, yielding 4,6-dihydroxy-5-benzylthiopyrimidine (2) with a variable yield, the best being 50%. Finally, compound (2) was converted to the title compound (3) by heating in phosphorus oxychloride, resulting in a 75% yield. An improved method was developed using sulfenyl chloride chemistry, where benzyl sulfenyl chloride was prepared from dibenzyl disulfide and sulfuryl chloride, and reacted with 4,6-dihydroxypyrimidine (1) in N,N-dimethylformamide to obtain compound (2) in quantitative yield. The title compound (3) was then synthesized from compound (2) using phosphorus oxychloride, achieving an overall yield of approximately 72%. The study provides a more efficient and reliable synthesis route for 4,6-dichloro-5-benzylthiopyrimidine, which is a key precursor in the synthesis of various types of 4,6-di-substituted pyrimidine-5-sulfonamides with interesting biological activities.

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