2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-

Base Information

• Chemical Name: 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-
• CAS No.: 130351-63-2
• Molecular Formula: C₁₂H₁₅BrN₂O₆
• Molecular Weight: 363.165
• Nikkaji Number: J343.692F
• Mol file: 130351-63-2.mol

Synonyms:3'-Hydroxymethyl Ara-5-Br-vinyl-U;130351-63-2;(E)-5-(2-Bromovinyl)-1-(3-deoxy-3-C-(hydroxymethyl)-beta-D-arabino-pentofuranosyl uracil;2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-;SCHEMBL4952193;1-(3-Deoxy-3-hydroxymethyl-beta-D-arabinofuranosyl)-5-[(E)-2-bromoethenyl]uracil;(E)-5-(2-Bromovinyl)-1-[3-deoxy-3-C-(hydroxymethyl)-.beta.-D-arabino-pentofuranosyl uracil;2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-[3-deoxy-3-(hydroxymethyl)-.beta.-D-arabinofuranosyl]-, (E)-;5-[(E)-2-bromovinyl]-1-[(2R,3S,4S,5S)-3-hydroxy-4,5-bis(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Chemical Property of 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-

Chemical Property:

• Density: 1.834g/cm³
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 362.01135
• Heavy Atom Count: 21
• Complexity: 494

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)CO)O)C=CBr
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)CO)O)/C=C/Br

Technology Process of 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)-

There total 10 articles about 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-1-(3-deoxy-3-(hydroxymethyl)-beta-D-arabinofuranosyl)-, (E)- 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: 51.0%

(E)-5-(2-carboxyvinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil (130351-62-1) → (E)-5-(2-bromovinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil (130351-63-2)

Guidance literature:

With N-Bromosuccinimide; potassium carbonate; In N,N-dimethyl-formamide; for 0.5h; Ambient temperature;

DOI:10.1021/jm00171a025

Reference yield:

1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil (130351-52-9) → (E)-5-(2-bromovinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil (130351-63-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 °C

3: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature

4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h

5: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating

6: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating

7: 55 percent / aq. NaOH / Ambient temperature

8: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; tetrabutyl ammonium fluoride; iodine; nitric acid; palladium diacetate; potassium carbonate; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00171a025

Reference yield:

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione (96253-10-0) → (E)-5-(2-bromovinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil (130351-63-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min

2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature

3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 °C

5: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature

6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h

7: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating

8: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating

9: 55 percent / aq. NaOH / Ambient temperature

10: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; iodine; nitric acid; palladium diacetate; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jm00171a025

upstream raw materials:

(E)-5-(2-carboxyvinyl)-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil

1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil

(E)-5-<2-(carbomethoxy)vinyl>-1-<3-deoxy-3-C-(hydroxymethyl)-β-D-arabino-pentofuranosyl>uracil

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione