1-(2-deoxy-β-D-ribofuranosyl)-N⁶-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione

Base Information

• Chemical Name: 1-(2-deoxy-β-D-ribofuranosyl)-N⁶-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione
• CAS No.: 597551-63-8
• Molecular Formula: C₂₁H₁₉N₅O₇
• Molecular Weight: 453.411

Synonyms:1-(2-deoxy-β-D-ribofuranosyl)-N⁶-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione

Chemical Property of 1-(2-deoxy-β-D-ribofuranosyl)-N⁶-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 1-(2-deoxy-β-D-ribofuranosyl)-N⁶-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione

There total 9 articles about 1-(2-deoxy-β-D-ribofuranosyl)-N⁶-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione 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: 83.0%

1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)-N6-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione (597551-62-7) → 1-(2-deoxy-β-D-ribofuranosyl)-N6-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione (597551-63-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ja0347686

Reference yield:

5-amino-1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)imidazole-4-carbonitrile (597551-53-6) → 1-(2-deoxy-β-D-ribofuranosyl)-N6-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione (597551-63-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 57 percent / diiodomethane; isoamyl nitrite / CHCl₃ / Heating

2: 81 percent / dba3Pd₂*CHCl₃ / dimethylformamide / 100 °C

3: 92 percent / aq. H₂O₂; NH₄OH / methanol / 13 h / 20 °C

4: 51 percent / isoamyl nitrite / tetrahydrofuran; H₂O / 3 h / 60 °C

5: 73 percent / NH₃ / methanol / 48 h / 120 °C

6: 64 percent / pyridine / 2.5 h / 20 °C

7: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ammonium hydroxide; diiodomethane; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; isopentyl nitrite; In tetrahydrofuran; methanol; chloroform; water; N,N-dimethyl-formamide; 2: Stille coupling;

DOI:10.1021/ja0347686

Reference yield:

1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)-5-iodoimidazole-4-carbonitrile (597551-55-8) → 1-(2-deoxy-β-D-ribofuranosyl)-N6-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione (597551-63-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / dba3Pd₂*CHCl₃ / dimethylformamide / 100 °C

2: 92 percent / aq. H₂O₂; NH₄OH / methanol / 13 h / 20 °C

3: 51 percent / isoamyl nitrite / tetrahydrofuran; H₂O / 3 h / 60 °C

4: 73 percent / NH₃ / methanol / 48 h / 120 °C

5: 64 percent / pyridine / 2.5 h / 20 °C

6: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ammonium hydroxide; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; isopentyl nitrite; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1: Stille coupling;

DOI:10.1021/ja0347686

upstream raw materials:

1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)-N⁶-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione

1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)-5-iodoimidazole-4-carbonitrile

5-amino-1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)imidazole-4-carbonitrile

5-amino-1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)imidazole-4-carboxamide

Downstream raw materials:

1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N⁶-(4-methoxybenzoyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine-4,7(5H)-dione

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