2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Base Information

• Chemical Name: 2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one
• CAS No.: 444019-16-3
• Molecular Formula: C₃₂H₃₂N₄O₆
• Molecular Weight: 568.629

Synonyms:2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Chemical Property of 2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

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Technology Process of 2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

There total 8 articles about 2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-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:

2-{[(4-Methoxy-phenyl)-diphenyl-methyl]-amino}-7-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one → 2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (444019-16-3)

Guidance literature:

With triethylamine trihydrofluoride; triethylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jm0495172

Reference yield:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → 2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (444019-16-3)

Guidance literature:

Multi-step reaction with 7 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: NaH / dimethylformamide / 0.5 h / 15 °C

3.2: 80 percent / dimethylformamide / 16 h / 20 °C

4.1: 86 percent / aq. NaOH / 7 h / Heating

5.1: 85 percent / pyridine / 20 °C

6.1: DMAP; pyridine / 20 °C

7.1: 0.72 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C

With pyridine; dmap; sodium hydroxide; Dowex WX₈-400; triethylamine trihydrofluoride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm0495172

Reference yield:

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1) → 2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (444019-16-3)

Guidance literature:

Multi-step reaction with 7 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: NaH / dimethylformamide / 0.5 h / 15 °C

3.2: 80 percent / dimethylformamide / 16 h / 20 °C

4.1: 86 percent / aq. NaOH / 7 h / Heating

5.1: 85 percent / pyridine / 20 °C

6.1: DMAP; pyridine / 20 °C

7.1: 0.72 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C

With pyridine; dmap; sodium hydroxide; Dowex WX₈-400; triethylamine trihydrofluoride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 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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