1-Allyl-5-fluorouracil

Base Information

• Chemical Name: 1-Allyl-5-fluorouracil
• CAS No.: 4871-14-1
• Molecular Formula: C7H7 F N2 O2
• Molecular Weight: 170.143
• NSC Number: 379685
• DSSTox Substance ID: DTXSID50321676
• Nikkaji Number: J2.136.009K
• Wikidata: Q82079716
• Mol file: 4871-14-1.mol

Synonyms:1-Allyl-5-fluorouracil;4871-14-1;1-Allyl-5-fluoropyrimidine-2,4(1H,3H)-dione;NSC379685;ST4044695;SCHEMBL17791229;DTXSID50321676;STK759783;AKOS001741142;NSC 379685;NSC-379685;EU-0018519;1-allyl-5-fluoro-2,4(1H,3H)-pyrimidinedione;SR-01000523452;SR-01000523452-1;5-fluoro-1-(prop-2-en-1-yl)pyrimidine-2,4(1H,3H)-dione

Chemical Property of 1-Allyl-5-fluorouracil

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.32g/cm³
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 170.04915563
• Heavy Atom Count: 12
• Complexity: 273

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCN1C=C(C(=O)NC1=O)F

Technology Process of 1-Allyl-5-fluorouracil

There total 7 articles about 1-Allyl-5-fluorouracil 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: 54.0%

5-fluorouracil (51-21-8) + allyl alcohol (107-18-6) → 1-allyl-5-fluoro-2,4(1H,3H)-pyrimidinedione (4871-14-1)

Guidance literature:

With potassium carbonate; triethylamine; In N,N-dimethyl-formamide; for 8h; Heating;

DOI:10.1016/j.tet.2007.11.101

Reference yield: 48.5%

allyl bromide (106-95-6) + 5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine (17242-85-2) → 1-allyl-5-fluoro-2,4(1H,3H)-pyrimidinedione (4871-14-1)

Guidance literature:

In acetonitrile; 1) room temp., 2 h; 2) reflux, 2 h; 3) room temp., overnight.;

DOI:10.1135/cccc19803217

Reference yield: 47.0%

5-fluorouracil (51-21-8) + allyl bromide (106-95-6) → 1-allyl-5-fluoro-2,4(1H,3H)-pyrimidinedione (4871-14-1)

Guidance literature:

5-fluorouracil; With potassium carbonate; In N,N-dimethyl-formamide; for 0.5h;

allyl bromide; In N,N-dimethyl-formamide; at 50 ℃; for 12h;

DOI:10.1021/acs.jmedchem.0c01435

upstream raw materials:

5-fluorouracil

allyl bromide

Carbonic acid 3-allyl-5-fluoro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester benzyl ester

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

Downstream raw materials:

5-fluorouracil

5-fluoro-1-({(3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl}methyl)pyrimidine-2,4(1H,3H)-dione

ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate