N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide

Base Information

• Chemical Name: N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide
• CAS No.: 281676-42-4
• Molecular Formula: C₃₂H₃₁N₅O₆
• Molecular Weight: 581.628
• Mol file: 281676-42-4.mol

Synonyms:N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide

Chemical Property of N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide

There total 6 articles about N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide 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: 73.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-(2-deoxy-β-D-erythro-pentofuranosyl)-N-[(dimethylamino)methylidene]-1H-pyrazolo[3,4-d]pyrimidin-6-amine (287177-84-8) → N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide (281676-42-4)

Guidance literature:

With pyridine; dmap; for 4h;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<928::AID-HLCA928>3.0.CO;2-5

Reference yield:

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride (3056-12-0,3601-89-6,4330-21-6,52304-86-6,141846-57-3) → N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide (281676-42-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 40 percent / 30 percent aq KOH / tetrahydrofuran / 0.03 h

2: hydrogen; Et₃N / 10 percent Pd/C / tetrahydrofuran / 3 h / 20 °C

3: NaOMe / methanol / 1 h / 20 °C

4: 73 percent / dimethylformamide / 2 h / 20 °C

5: 73 percent / pyridine; 4-(dimethylamino)pyridine / 4 h

With pyridine; dmap; potassium hydroxide; hydrogen; sodium methylate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Reduction / 3: Hydrolysis / 4: Substitution / 5: Substitution;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<928::AID-HLCA928>3.0.CO;2-5

Reference yield:

4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine (100644-65-3) → N-{1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}formamide (281676-42-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 40 percent / 30 percent aq KOH / tetrahydrofuran / 0.03 h

2: hydrogen; Et₃N / 10 percent Pd/C / tetrahydrofuran / 3 h / 20 °C

3: NaOMe / methanol / 1 h / 20 °C

4: 73 percent / dimethylformamide / 2 h / 20 °C

5: 73 percent / pyridine; 4-(dimethylamino)pyridine / 4 h

With pyridine; dmap; potassium hydroxide; hydrogen; sodium methylate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Reduction / 3: Hydrolysis / 4: Substitution / 5: Substitution;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<928::AID-HLCA928>3.0.CO;2-5

upstream raw materials:

4,4'-dimethoxytrityl chloride

1-(2-deoxy-β-D-erythro-pentofuranosyl)-N-[(dimethylamino)methylidene]-1H-pyrazolo[3,4-d]pyrimidin-6-amine

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride

4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine