7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one

Base Information

• Chemical Name: 7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS No.: 1440175-13-2
• Molecular Formula: C₄₉H₅₀N₄O₇S
• Molecular Weight: 839.025

Synonyms:7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one

Chemical Property of 7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one

Chemical Property:

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Technology Process of 7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one

There total 6 articles about 7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one 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: 65.0%

4,4,5,5-tetramethyl-2-(2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-enyl)-1,3,2-dioxaborolane (1229936-73-5) + 7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodo-6-methyl-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one (1440175-06-3) → 7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one (1440175-13-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; triethylamine; In tetrahydrofuran; water; for 24h; Schlenk technique; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201300261

Reference yield:

2-amino-6-methyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (204929-06-6) → 7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one (1440175-13-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 3.5 h / 20 °C / Inert atmosphere

2.1: N-iodo-succinimide / dichloromethane / 0.5 h / 40 °C / Inert atmosphere

3.1: sodium hydride / acetonitrile; mineral oil / 0.25 h / 0 °C / Inert atmosphere

3.2: 1.5 h / 20 °C / Inert atmosphere

4.1: cesium acetate; 1,4-diaza-bicyclo[2.2.2]octane; triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

5.1: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; tetrahydrofuran / 24 h / Schlenk technique; Inert atmosphere; Reflux

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; N-iodo-succinimide; cesium acetate; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 5.1: |Suzuki Coupling;

DOI:10.1002/ejoc.201300261

Reference yield:

4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine (1440174-97-9) → 7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-methyl-5-[2-(2-methyl-5-phenylthien-3-yl)cyclopent-1-enyl]-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one (1440175-13-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-iodo-succinimide / dichloromethane / 0.5 h / 40 °C / Inert atmosphere

2.1: sodium hydride / acetonitrile; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 1.5 h / 20 °C / Inert atmosphere

3.1: cesium acetate; 1,4-diaza-bicyclo[2.2.2]octane; triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

4.1: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; tetrahydrofuran / 24 h / Schlenk technique; Inert atmosphere; Reflux

With 1,4-diaza-bicyclo[2.2.2]octane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; N-iodo-succinimide; cesium acetate; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 4.1: |Suzuki Coupling;

DOI:10.1002/ejoc.201300261

upstream raw materials:

4,4,5,5-tetramethyl-2-(2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-enyl)-1,3,2-dioxaborolane

7-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodo-6-methyl-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidin-4-one

2-amino-6-methyl-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidine

2-amino-6-methyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

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