2,4(1H,3H)-Pyrimidinedione, 5-((E)-2-bromoethenyl)-1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-

Base Information

Chemical Name:2,4(1H,3H)-Pyrimidinedione, 5-((E)-2-bromoethenyl)-1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-
CAS No.:120963-50-0
Molecular Formula:C₁₂H₁₅BrN₂O₄
Molecular Weight:331.166
Hs Code.:
ChEMBL ID:CHEMBL341644
Mol file:120963-50-0.mol

Synonyms:1-(3-hydroxy-4-(hydroxymethyl)-cyclopentyl)-5-(2-bromovinyl)-2,4-(1H,3H)-pyrimidinedione;C-BVDU;carbocyclic 5-(2-bromovinyl)-2'--deoxyuridine;carbocyclic BVDU

Suppliers and Price of 2,4(1H,3H)-Pyrimidinedione, 5-((E)-2-bromoethenyl)-1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2,4(1H,3H)-Pyrimidinedione, 5-((E)-2-bromoethenyl)-1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-

Chemical Property:

Boiling Point:°Cat760mmHg
Flash Point:°C
Density:1.758g/cm³
XLogP3:0.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:330.02152
Heavy Atom Count:19
Complexity:449

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1C(CC(C1CO)O)N2C=C(C(=O)NC2=O)C=CBr
Isomeric SMILES:C1[C@@H](C[C@H]([C@@H]1CO)O)N2C=C(C(=O)NC2=O)/C=C/Br

Technology Process of 2,4(1H,3H)-Pyrimidinedione, 5-((E)-2-bromoethenyl)-1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-

There total 31 articles about 2,4(1H,3H)-Pyrimidinedione, 5-((E)-2-bromoethenyl)-1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)- 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: 62.0%

: 91661-15-3,91739-45-6,120963-48-6,120963-49-7
(E)-3-[1-((1S,3S,4S)-3-Hydroxy-4-hydroxymethyl-cyclopentyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylic acid

: 91661-22-2,95463-56-2,103302-21-2,103302-22-3,103476-38-6,120963-50-0
5-((E)-2-Bromo-vinyl)-1-((1S,3S,4S)-3-hydroxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

Guidance literature:: With N-Bromosuccinimide; potassium hydrogencarbonate; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;
DOI:10.1039/c39900001547

Reference yield:

: 120963-35-1
(+)-(1S,2S,4S)-4-<(benzyloxy)methyl>-2-hydroxycyclopentanemethanol

: 120963-50-0
(-)-1-<(1S,3R,4S)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 12 steps

1: 99 percent / pyridine / CH₂Cl₂ / 0.17 h

2: 90 percent / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

3: 58 percent / dimethylsulfoxide / 40 - 45 °C

4: 100 percent / H₂ / 5percent Pd/C / ethanol / 3000.2 Torr

5: 85 percent / pyridinium dichromate (PDC) / dimethylformamide / 30 h / Ambient temperature

6: 1.) diphenyl phosphorazidate, 2.) NH₃ / 1.) benzene, reflux, 45 min, 2.) room temperature

7: 68 percent / pyridine / CH₂Cl₂ / Ambient temperature

8: 85 percent / conc. aq. ammonia / 4 h / 90 °C

9: 75 percent / I₂, 0.75 N HNO₃ / dioxane / 1 h / Heating

10: 72 percent / Et₃N, Ph₃P / Pd(OAc)2 / dioxane / 85 °C

11: 71.4 percent / KOH / H₂O / 2 h / Ambient temperature

12: 1.) KHCO₃, 2.) N-bromosuccinimide / 1.) DMF, room temperature, 5 min, 2.) DMF, 90 min

With pyridine; potassium hydroxide; ammonium hydroxide; N-Bromosuccinimide; dipyridinium dichromate; diphenyl phosphoryl azide; ammonia; hydrogen; iodine; nitric acid; potassium hydrogencarbonate; triethylamine; triphenylphosphine; palladium diacetate; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm00128a029

Reference yield:

: (+)-(1S,6S,8S)-3-phenyl-2,4-dioxabicyclo<4.3.0>nonane-8-methanol

: 120963-50-0
(-)-1-<(1S,3R,4S)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) KH / 1.) THF, room temperature, 20 min, 2.) 12 h

2: 98 percent / conc. H₂SO₄ / H₂O / 0.17 h / Heating

3: 99 percent / pyridine / CH₂Cl₂ / 0.17 h

4: 90 percent / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

5: 58 percent / dimethylsulfoxide / 40 - 45 °C

6: 100 percent / H₂ / 5percent Pd/C / ethanol / 3000.2 Torr

7: 85 percent / pyridinium dichromate (PDC) / dimethylformamide / 30 h / Ambient temperature

8: 1.) diphenyl phosphorazidate, 2.) NH₃ / 1.) benzene, reflux, 45 min, 2.) room temperature

9: 68 percent / pyridine / CH₂Cl₂ / Ambient temperature

10: 85 percent / conc. aq. ammonia / 4 h / 90 °C

11: 75 percent / I₂, 0.75 N HNO₃ / dioxane / 1 h / Heating

12: 72 percent / Et₃N, Ph₃P / Pd(OAc)2 / dioxane / 85 °C

13: 71.4 percent / KOH / H₂O / 2 h / Ambient temperature

14: 1.) KHCO₃, 2.) N-bromosuccinimide / 1.) DMF, room temperature, 5 min, 2.) DMF, 90 min

With pyridine; potassium hydroxide; ammonium hydroxide; N-Bromosuccinimide; dipyridinium dichromate; sulfuric acid; diphenyl phosphoryl azide; ammonia; hydrogen; iodine; nitric acid; potassium hydride; potassium hydrogencarbonate; triethylamine; triphenylphosphine; palladium diacetate; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm00128a029