1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-2-phenylethenyl]pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-2-phenylethenyl]pyrimidine-2,4-dione
• CAS No.: 72045-17-1
• Molecular Formula: C17H18N2O5
• Molecular Weight: 330.34
• NSC Number: 317848
• Mol file: 72045-17-1.mol

Synonyms:NSC317848;72045-17-1;NSC-317848

Chemical Property of 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-2-phenylethenyl]pyrimidine-2,4-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.468g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 330.12157168
• Heavy Atom Count: 24
• Complexity: 553

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C=CC3=CC=CC=C3)CO)O
• Isomeric SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)/C=C/C3=CC=CC=C3)CO)O

Technology Process of 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-2-phenylethenyl]pyrimidine-2,4-dione

There total 8 articles about 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-2-phenylethenyl]pyrimidine-2,4-dione 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: 82.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 5-<(E)-2-phenylethenyl>-2'-deoxyuridine (72045-17-1)

Guidance literature:

With palladium diacetate; triethylamine; In water; acetonitrile; at 80 ℃; Inert atmosphere;

DOI:10.1055/s-0031-1289886

Reference yield: 65.0%

(E)-5-(2-bromovinyl)-2'-deoxyuridine (69304-47-8) + phenylboronic acid (98-80-6) → 5-<(E)-2-phenylethenyl>-2'-deoxyuridine (72045-17-1)

Guidance literature:

(E)-5-(2-bromovinyl)-2'-deoxyuridine; With [Pd(succinimidate)2(1,3,5-triaza-7-phosphaadamantane)2]; In water; at 80 ℃; for 0.0833333h; Inert atmosphere;

phenylboronic acid; With triethylamine; In water; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1021/acs.joc.5b02475

Reference yield: 57.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + C5-chloromercuri-2'-deoxyuridine (65505-76-2) → 5-<(E)-2-phenylethenyl>-2'-deoxyuridine (72045-17-1)

Guidance literature:

With lithium pentachloropalladate; In methanol; for 12h; Heating;

DOI:10.1021/ja00526a044

upstream raw materials:

styrene

C⁵-chloromercuri-2'-deoxyuridine

2'-deoxyuridine

trans-2-phenylvinylboronic acid