1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

Base Information

• Chemical Name: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
• CAS No.: 7226-23-5
• Molecular Formula: C6H12N2O
• Molecular Weight: 128.174
• Hs Code.: 29335995
• European Community (EC) Number: 230-625-6
• DSSTox Substance ID: DTXSID3074575
• Nikkaji Number: J35.422H
• Wikipedia: DMPU
• Wikidata: Q416637
• ChEMBL ID: CHEMBL12284
• Mol file: 7226-23-5.mol

Synonyms:N,N'-dimethylpropyleneurea

Chemical Property of 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellowish liquid
• Vapor Pressure: 0.082mmHg at 25°C
• Melting Point: -20 °C
• Refractive Index: n20/D 1.488(lit.)
• Boiling Point: 240.2 °C at 760 mmHg
• PKA: -0.65±0.20(Predicted)
• Flash Point: 85.3 °C
• PSA: 23.55000
• Density: 1.024 g/cm³
• LogP: 0.24950
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: soluble
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 128.094963011
• Heavy Atom Count: 9
• Complexity: 112

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-43-62-41
• Safety Statements: 23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrimidines
• Canonical SMILES: CN1CCCN(C1=O)C
• Uses: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is a versatile organic solvent in and less toxic than HMPA. It is mainly applied in the synthesis of pharmaceuticals and agrochemicals. DMPU is also used in the electronics industry. 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is a versatile solvent used in the N-alkylation of chiral and O-alkylation of aldoses. It is involved in the preparation of poly(aryl ethers). It is a cyclic urea and used as a polar aprotic organic solvent. Further, it reacts with trifluoro-methanesulfonic acid anhydride to prepare 2,2'-oxy-bis(1,3-dimethyl-tetrahydropyrimidinium) bis(trifluoromethanesulfonate). Versatile solvent employed in N-alkylation of chiral, primary amines, O-alkylation of aldoses, and in the synthesis of poly(aryl ethers).

Technology Process of 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

There total 19 articles about 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone 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: 94.0%

carbon monoxide (201230-82-2) + 1,3-bis(methylamino)propane (111-33-1) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Guidance literature:

carbon monoxide; 1,3-bis(methylamino)propane; With selenium; at 20 ℃; for 2h; under 750.075 Torr; neat (no solvent);

With oxygen; at 20 ℃; for 1h; under 750.075 Torr; neat (no solvent);

DOI:10.1055/s-0030-1258299

Reference yield: 90.0%

β-(4-hydroxyphenyl)ethyl iodoacetamide (53527-07-4) + 3-(((3-acetamido-4-methoxy-2-methyl-4-oxobutan-2-yl)disulfanecarbonyl)(methyl)amino)-N-methylpropan-1-aminium trifluoroacetate → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5) + β-(4-hydroxyphenyl)ethyl-2-aminoacetamide (55710-99-1) + methyl 2-acetamido-3-((2-((4-hydroxyphenethyl)amino)-2-oxoethyl)disulfaneyl)-3-methylbutanoate + C18H26N2O5S

Guidance literature:

With diethylenetriaminopentaacetic acid; In aq. buffer; at 37 ℃; for 7h; pH=7.4; Solvent; pH-value; Kinetics;

DOI:10.1021/jacs.9b12180

Reference yield: 81.0%

3,4,5,6-tetrahydropyrimidine-2-thione (2055-46-1) + methyl iodide (74-88-4) → 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7226-23-5)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; for 5h; Heating;

DOI:10.1055/s-1982-29837

upstream raw materials:

2-(methylthio)-1,4,5,6-tetrahydropyrimidine

methyl iodide

3,4,5,6-tetrahydropyrimidin-2(1H)-one

dimethyl sulfate

Downstream raw materials:

4-Methoxybenzyl alcohol

1-[[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]sulfonyl]-2,4-imidazolidinedione

1-N,N-dimethylcarbamoyl-6-(4-fluorophenyl)-3-{4-[(1H-2-methylimidazo[4.5-c]pyrid-1-yl)methyl]benzoyl}indole

Refernces

• 1、 Filgueiras,Huheey. "-". . p. 49,51,52. Retrieved 1976.
• 2、 Belvisi, Laura,Borlandelli, Valentina,Corno, Cristina,Dal Corso, Alberto,Gennari, Cesare,Perego, Paola,Pignataro, Luca. "Fast Cyclization of a Proline-Derived Self-Immolative Spacer Improves the Efficacy of Carbamate Prodrugs". . p. 4176 - 4181. Retrieved 2020/02/05.
• 3、 Mizuno, Takumi,Nakai, Takeo,Mihara, Masatoshi. "Efficient solvent-free synthesis of urea derivatives using selenium-catalyzed carbonylation of amines with carbon monoxide and oxygen". experimental part. p. 4251 - 4255. Retrieved 2011/03/17.