(6R)-2-(1,1-Dimethylethyl)-5,6-dihydro-6-(4-methoxyphenyl)-4(3H)-pyrimidinone

Base Information

• Chemical Name: (6R)-2-(1,1-Dimethylethyl)-5,6-dihydro-6-(4-methoxyphenyl)-4(3H)-pyrimidinone
• CAS No.: 131791-83-8
• Molecular Formula: C15H20N2O2
• Molecular Weight: 260.336
• DSSTox Substance ID: DTXSID201139238
• Mol file: 131791-83-8.mol

Synonyms:DTXSID201139238;(6R)-2-(1,1-Dimethylethyl)-5,6-dihydro-6-(4-methoxyphenyl)-4(3H)-pyrimidinone;131791-83-8

Chemical Property of (6R)-2-(1,1-Dimethylethyl)-5,6-dihydro-6-(4-methoxyphenyl)-4(3H)-pyrimidinone

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 260.152477885
• Heavy Atom Count: 19
• Complexity: 363

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C1=NC(CC(=O)N1)C2=CC=C(C=C2)OC
• Isomeric SMILES: CC(C)(C)C1=N[C@H](CC(=O)N1)C2=CC=C(C=C2)OC

Technology Process of (6R)-2-(1,1-Dimethylethyl)-5,6-dihydro-6-(4-methoxyphenyl)-4(3H)-pyrimidinone

There total 1 articles about (6R)-2-(1,1-Dimethylethyl)-5,6-dihydro-6-(4-methoxyphenyl)-4(3H)-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: 78.0%

para-iodoanisole (696-62-8) + (S)-2-tert-butyl-1-carbomethoxy-2,3-dihydro-4(1H)-pyrimidinone (131791-75-8) → (S)-2-tert-Butyl-6-(4-methoxyphenyl)-5,6-dihydro-4-(1H)-pyrimidinone (131791-83-8)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; for 24h; Heating;

DOI:10.1021/jo00017a037

Reference yield: 65.0%

(S)-2-tert-Butyl-6-(4-methoxyphenyl)-5,6-dihydro-4-(1H)-pyrimidinone (131791-83-8) → (R)-2-tert-Butyl-6-(4-methoxy-phenyl)-tetrahydro-pyrimidin-4-one (134781-90-1)

Guidance literature:

With hydrogenchloride; sodium tetrahydroborate; In tetrahydrofuran; ethanol; 1.) pH 7, -35 deg C, 1 h, 2.) -20 deg C, overnight;

DOI:10.1021/jo00017a037

Reference yield:

(S)-2-tert-Butyl-6-(4-methoxyphenyl)-5,6-dihydro-4-(1H)-pyrimidinone (131791-83-8) → (R)-β-amino-β-(4-methoxyphenyl)propionic acid (131690-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NaBH₄, 9 N HCl / tetrahydrofuran; aq. ethanol / 1.) pH 7, -35 deg C, 1 h, 2.) -20 deg C, overnight

2: 81 percent / 4.5 N HCl / 2.5 h / 100 °C

With hydrogenchloride; sodium tetrahydroborate; In tetrahydrofuran; ethanol;

DOI:10.1021/jo00017a037

upstream raw materials:

para-iodoanisole

(S)-2-tert-butyl-1-carbomethoxy-2,3-dihydro-4(1H)-pyrimidinone

Downstream raw materials:

methyl (-)-(3R)-3-amino-3-(4-methoxyphenyl)propanoate

(R)-2-tert-Butyl-6-(4-methoxy-phenyl)-tetrahydro-pyrimidin-4-one

jasplakinolide

N-Boc-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester