2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine

Base Information

• Chemical Name: 2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine
• CAS No.: 864155-91-9
• Molecular Formula: C₄₀H₃₁Cl₂N₃O₇
• Molecular Weight: 736.608

Synonyms:2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine

Chemical Property of 2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine

Chemical Property:

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Technology Process of 2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine

There total 6 articles about 2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine 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: 95.0%

2,4-dichloro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine (864155-82-8) + 4-Methylbenzyl bromide (104-81-4) → 2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine (864155-91-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃;

DOI:10.1081/NCN-200046784

Reference yield:

2-amino-3-benzyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one (864155-79-3) → 2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine (864155-91-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / cyclohexene / palladium(II) hydroxide on carbon / ethanol / 120 - 125 °C

2: 40 percent / phosphorus oxychloride; benzyltriethylammonium chloride; N,N-dimethylaniline / acetonitrile / 0.5 h / Heating

3: 71 percent / tert-butyl nitrite; antimony trichloride / 1,2-dichloro-ethane / 4 h / -10 °C

4: 95 percent / 1,8-diaza-bicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C

With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) chloride; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; cyclohexene; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1081/NCN-200046784

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (14215-97-5) → 2,4-dichloro-5-(p-methylbenzyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine (864155-91-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / tin(IV) chloride / nitromethane / 3 h / 55 - 60 °C

2: 78 percent / cyclohexene / palladium(II) hydroxide on carbon / ethanol / 120 - 125 °C

3: 40 percent / phosphorus oxychloride; benzyltriethylammonium chloride; N,N-dimethylaniline / acetonitrile / 0.5 h / Heating

4: 71 percent / tert-butyl nitrite; antimony trichloride / 1,2-dichloro-ethane / 4 h / -10 °C

5: 95 percent / 1,8-diaza-bicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C

With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) chloride; tin(IV) chloride; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; cyclohexene; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; nitromethane; ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1081/NCN-200046784

upstream raw materials:

2,4-dichloro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine

4-Methylbenzyl bromide

2-amino-4-chloro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine

2-amino-3-benzyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one

Downstream raw materials:

4-amino-2-chloro-5-(p-methylbenzyl)-7-β-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidine

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