2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Base Information

• Chemical Name: 2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one
• CAS No.: 444019-20-9
• Molecular Formula: C₃₁H₃₀N₄O₅
• Molecular Weight: 538.603

Synonyms:2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Chemical Property of 2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

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Technology Process of 2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

There total 9 articles about 2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-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:

Acetic acid (2R,3R,5S)-5-acetoxymethyl-2-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-4-oxo-3,4-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-tetrahydro-furan-3-yl ester → 2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (444019-20-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 18h;

DOI:10.1021/jm0495172

Reference yield:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → 2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (444019-20-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / acetonitrile / 0.5 h / 15 °C

1.2: hexamethylphosphorus triamide / acetonitrile; tetrahydrofuran; CCl₄ / 16 h

2.1: 10.7 g / Dowex WX₈-400 / methanol; H₂O / 16 h / 20 °C

3.1: α-acetoxyisobutyryl bromide / acetonitrile; H2O / 2 h / 20 °C

3.2: 94 percent / Dowex OH^- resin

4.1: 60 percent / LiEt₃BH / tetrahydrofuran / 4 h / 0 °C

5.1: 80 percent / aq. NaOH / 3 h / Heating

6.1: 95 percent / DMAP; Et₃N / acetonitrile / 5 h / 20 °C

7.1: 84 percent / pyridine / 20 °C

8.1: 0.73 g / aq. NaOH / dioxane / 18 h / 20 °C

With pyridine; dmap; sodium hydroxide; Dowex WX₈-400; acetoxyisobutyryl bromide; sodium hydride; lithium triethylborohydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile;

DOI:10.1021/jm0495172

Reference yield:

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1) → 2-[(p-anisyldiphenylmethyl)amino]-7-(3-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (444019-20-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / acetonitrile / 0.5 h / 15 °C

1.2: hexamethylphosphorus triamide / acetonitrile; tetrahydrofuran; CCl₄ / 16 h

2.1: 10.7 g / Dowex WX₈-400 / methanol; H₂O / 16 h / 20 °C

3.1: α-acetoxyisobutyryl bromide / acetonitrile; H2O / 2 h / 20 °C

3.2: 94 percent / Dowex OH^- resin

4.1: 60 percent / LiEt₃BH / tetrahydrofuran / 4 h / 0 °C

5.1: 80 percent / aq. NaOH / 3 h / Heating

6.1: 95 percent / DMAP; Et₃N / acetonitrile / 5 h / 20 °C

7.1: 84 percent / pyridine / 20 °C

8.1: 0.73 g / aq. NaOH / dioxane / 18 h / 20 °C

With pyridine; dmap; sodium hydroxide; Dowex WX₈-400; acetoxyisobutyryl bromide; sodium hydride; lithium triethylborohydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile;

DOI:10.1021/jm0495172

upstream raw materials:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

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

4-chloro-7-{5′-O-[(1,1-dimethylethyl)-dimethylsilyl]-2′,3′-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine-2-amine

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