2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl-, (R)-

Base Information

• Chemical Name: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl-, (R)-
• CAS No.: 2303-80-2
• Molecular Formula: C13H14 N2 O3
• Molecular Weight: 246.2619
• UNII: M1V54MNO1P
• DSSTox Substance ID: DTXSID00177584
• Nikkaji Number: J367.447I
• Wikidata: Q83047905
• ChEMBL ID: CHEMBL253331
• Mol file: 2303-80-2.mol

Synonyms:(-)-Methylphenobarbital;Methylphenobarbital, (R)-;M1V54MNO1P;2303-80-2;2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl-, (R)-;(5R)-5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione;UNII-M1V54MNO1P;BIDD:PXR0006;CHEMBL253331;SCHEMBL11789851;DTXSID00177584;(-)-1-METHYLPHENOBARBITAL;(+/-)-5-Ethyl-1-methyl-5-phenylpyrimidine-2,4,6-trione;(R,S)-5-Ethyl-1-methyl-5-phenyl-pyrimidine-2,4,6-trione;2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-1-METHYL-5-PHENYL-, (5R)-

Chemical Property of 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl-, (R)-

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.211g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 246.10044231
• Heavy Atom Count: 18
• Complexity: 388

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C(=O)NC(=O)N(C1=O)C)C2=CC=CC=C2
• Isomeric SMILES: CC[C@]1(C(=O)NC(=O)N(C1=O)C)C2=CC=CC=C2

Technology Process of 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl-, (R)-

There total 9 articles about 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl-, (R)- 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:

Propionic acid (S)-5-ethyl-3-methyl-2,4,6-trioxo-5-phenyl-tetrahydro-pyrimidin-1-ylmethyl ester → (-)-Mephobarbital (2303-80-2)

Guidance literature:

With water; potassium carbonate; In methanol; Yield given;

DOI:10.1016/S0040-4039(00)93597-4

Reference yield:

(S)(+)-5-ethyl-5-phenyl-1-(propionyloxymethyl)barbital (138548-35-3) → (-)-Mephobarbital (2303-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: (iso-Pr)2EtN / CH₂Cl₂ / 3 h / Ambient temperature

2: aq. K₂CO₃ / methanol / 3 h / Ambient temperature

With potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1248/cpb.40.2605

Reference yield:

1,3-bis(propionyloxymethyl)-5-ethyl-5-phenylbarbital (27506-81-6) → (-)-Mephobarbital (2303-80-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / diisopropyl ether; H₂O / 2 h / Ambient temperature; lipase AY from Candida rugosa

2: (iso-Pr)2EtN / CH₂Cl₂ / 3 h / Ambient temperature

3: aq. K₂CO₃ / methanol / 3 h / Ambient temperature

With potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; di-isopropyl ether; water;

DOI:10.1248/cpb.40.2605

upstream raw materials:

(5S)-5-ethyl-3-methyl-1-(methyl β-D-glucopyranosyluronate)-5-phenyl-2,4,6-(1H,3H,5H)-pyrimidinetrione

mephobarbital

(5S)-5-ethyl-1-(methyl β-D-glucopyranosyluronate)-5-phenyl-2,4,6-(1H,3H,5H)-pyrimidinetrione

phenobarbital