6-AMINO-2-(2-DEOXY-BETA-D-RIBOFURANOSYL)-2,5-DIHYDRO-4H-PYRAZOLO-[3,4-D]PYRIMIDIN-4-ONE

Base Information

• Chemical Name: 6-AMINO-2-(2-DEOXY-BETA-D-RIBOFURANOSYL)-2,5-DIHYDRO-4H-PYRAZOLO-[3,4-D]PYRIMIDIN-4-ONE
• CAS No.: 109737-94-2
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.244
• Mol file: 109737-94-2.mol

Synonyms:6-AMINO-2-(2-DEOXY-BETA-D-RIBOFURANOSYL)-2,5-DIHYDRO-4H-PYRAZOLO-[3,4-D]PYRIMIDIN-4-ONE

Chemical Property of 6-AMINO-2-(2-DEOXY-BETA-D-RIBOFURANOSYL)-2,5-DIHYDRO-4H-PYRAZOLO-[3,4-D]PYRIMIDIN-4-ONE

Chemical Property:

• PSA: 139.28000
• LogP: -1.07630

Purity/Quality:

≥ 95% ^*data from raw suppliers

6-Amino-2-(2-deoxy-β-D-ribofuranosyl)-2,5-dihydro-4H-pyrazolo-[3,4-d]-pyrimidin-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 6-Amino-2-(2-deoxy-β-D-ribofuranosyl)-2,5-dihydro-4H-pyrazolo-[3,4-d]-pyrimidin-4-one is a derivative of 4-Amino-6-methyl-8-(2-deoxy-β-D-ribofuranosyl)-7(8H)-pteridone (A615680), which is a highly fluorescent adenosine analogue, which in a dimethoxytrityl, phosphoramidite protected form, can be site-specifically inserted into oligonucleotides through a 3’,5’-phosphodiester linkage using an automated DNA synthesizer.

Technology Process of 6-AMINO-2-(2-DEOXY-BETA-D-RIBOFURANOSYL)-2,5-DIHYDRO-4H-PYRAZOLO-[3,4-D]PYRIMIDIN-4-ONE

There total 6 articles about 6-AMINO-2-(2-DEOXY-BETA-D-RIBOFURANOSYL)-2,5-DIHYDRO-4H-PYRAZOLO-[3,4-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: 66.0%

6-Amino-2-(2'-deoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2H-pyrazolo<3,4-d>pyrimidine (109737-93-1) → 6-Amino-2-(2'-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo<3,4-d>pyrimidin-4(5H)-one (109737-94-2)

Guidance literature:

With potassium hydroxide; In water; for 48h; Ambient temperature;

DOI:10.1002/hlca.19860690714

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) → 6-Amino-2-(2'-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo<3,4-d>pyrimidin-4(5H)-one (109737-94-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 13 percent / KOH / tetrahydrofuran; H₂O / 0.03 h / Ambient temperature

2: 69 percent / NaOMe / methanol / 2 h / Ambient temperature

3: 66 percent / KOH / H₂O / 48 h / Ambient temperature

With potassium hydroxide; sodium methylate; In tetrahydrofuran; methanol; water;

DOI:10.1002/hlca.19860690714

Reference yield:

2-amino-4,6-dichloropyrimidine-5-carboxaldehyde (5604-46-6) → 6-Amino-2-(2'-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo<3,4-d>pyrimidin-4(5H)-one (109737-94-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / hydrazine hydrate / tetrahydrofuran; H₂O / 0.17 h / 50 °C

2: 90 percent / methanol / 1 h / Heating

3: 13 percent / KOH / tetrahydrofuran; H₂O / 0.03 h / Ambient temperature

4: 69 percent / NaOMe / methanol / 2 h / Ambient temperature

5: 66 percent / KOH / H₂O / 48 h / Ambient temperature

With potassium hydroxide; sodium methylate; hydrazine hydrate; In tetrahydrofuran; methanol; water;

DOI:10.1002/hlca.19860690714

upstream raw materials:

6-Amino-2-(2'-deoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2H-pyrazolo<3,4-d>pyrimidine

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

2-amino-4,6-dichloropyrimidine-5-carboxaldehyde

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

Downstream raw materials:

6-amino-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

2-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-6-{[(dimethylamino)methylidene]amino}-2H-pyrazolo[3,4-d]pyrimidin-4-one