4-Chloro-5-methyl-7-(2-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 4-Chloro-5-methyl-7-(2-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• CAS No.: 443642-55-5
• Molecular Formula: C₁₃H₁₆ClN₃O₄
• Molecular Weight: 313.741
• Mol file: 443642-55-5.mol

Synonyms:4-CHLORO-5-METHYL-7-(2-C-METHYL-B-D-RIBOFURANOSYL)-7H-PYRROLO[2,3-D]PYRIMIDINE;

Chemical Property of 4-Chloro-5-methyl-7-(2-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Chemical Property:

• PSA: 100.63000
• LogP: 0.39470

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Chloro-5-methyl-7-(2-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

There total 8 articles about 4-Chloro-5-methyl-7-(2-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-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: 78.0%

4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (443642-54-4) → 4-chloro-5-methyl-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (443642-55-5)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 - -20 ℃; for 5.5h;

DOI:10.1021/jm040068f

Reference yield:

C12H13BrClN3O4 + Trimethylboroxine (823-96-1) → 4-chloro-5-methyl-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (443642-55-5)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; for 18h; Heating / reflux;

Reference yield:

(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol (168427-35-8) → 4-chloro-5-methyl-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (443642-55-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 72 h / 20 °C

2.1: 16.7 g / diethyl ether / 7 h / -30 - -15 °C

3.1: HBr; AcOH / CH₂Cl₂ / 4 h / 0 - 20 °C

4.1: NaH / acetonitrile / 2 h / 20 °C

4.2: 0.87 g / acetonitrile / 24 h / 20 °C

5.1: 78 percent / boron trichloride / CH₂Cl₂ / 5.5 h / -78 - -20 °C

With hydrogen bromide; boron trichloride; sodium hydride; Dess-Martin periodane; acetic acid; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jm040068f

upstream raw materials:

4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidine

(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol

3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-erythro-pentafuranos-2-ulose

(2S,3R,4R,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-ol

Downstream raw materials:

4-amino-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid