4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranose

Base Information

• Chemical Name: 4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranose
• CAS No.: 476371-76-3
• Molecular Formula: C17H19N5O4
• Molecular Weight: 357.369
• Mol file: 476371-76-3.mol

Synonyms:4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranose;4-AMino-3-benzyl-1H-pyrazolo[3,4-d]pyriMidine 1-β-D-Ribofuranose;4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-b-D-ribofuranose;3-(PhenylMethyl)-1-β-D-ribofuranosyl-1H-pyrazolo[3,4-d]pyriMidin-4-aMine;1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 3-(phenylmethyl)-1-β-D-ribofuranosyl-

Chemical Property of 4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranose

Chemical Property:

• Boiling Point: 691.2±55.0 °C(Predicted)
• PKA: 12.99±0.70(Predicted)
• PSA: 139.54000
• Density: 1.68±0.1 g/cm3(Predicted)
• LogP: 0.19200

Purity/Quality:

97% ^*data from raw suppliers

4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-b-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranose

There total 6 articles about 4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranose 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: 80.0%

1-((2S,3R,4S,5R)-3,4-dibenzoyl-5-benzoylmethyltetrahydrofuran-2-yl)-3-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (476371-72-9) → (2S,3R,4S,5R)-2-(4-amino-3-benzylpyrazolo[3,4-d]pyrimidin-1-yl)-5-hydroxymethyltetrahydrofuran-3,4-diol (476371-76-3)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 36h;

DOI:10.1021/ja0264798

Reference yield:

2-(1-Methoxy-2-phenylethylidene)malononitrile (42754-59-6) → (2S,3R,4S,5R)-2-(4-amino-3-benzylpyrazolo[3,4-d]pyrimidin-1-yl)-5-hydroxymethyltetrahydrofuran-3,4-diol (476371-76-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / hydrazine hydrochloride; triethylamine / ethanol / 0.25 h / Heating

2: 72 percent / 180 °C

3: 80 percent / SnCl₄ / acetonitrile / 5 h / 20 °C

4: 80 percent / NH₃ / methanol / 36 h / 20 °C

With hydrazine hydrochloride; ammonia; tin(IV) chloride; triethylamine; In methanol; ethanol; acetonitrile;

DOI:10.1021/ja0264798

Reference yield:

phenylacetyl chloride (103-80-0) → (2S,3R,4S,5R)-2-(4-amino-3-benzylpyrazolo[3,4-d]pyrimidin-1-yl)-5-hydroxymethyltetrahydrofuran-3,4-diol (476371-76-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran / 0 °C

1.2: 90 percent / tetrahydrofuran / 0 - 20 °C

2.1: 90 percent / aq. NaHCO₃ / dioxane / 2 h / Heating

3.1: 52 percent / hydrazine hydrochloride; triethylamine / ethanol / 0.25 h / Heating

4.1: 72 percent / 180 °C

5.1: 80 percent / SnCl₄ / acetonitrile / 5 h / 20 °C

6.1: 80 percent / NH₃ / methanol / 36 h / 20 °C

With hydrazine hydrochloride; ammonia; tin(IV) chloride; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; acetonitrile;

DOI:10.1021/ja0264798

upstream raw materials:

1-((2S,3R,4S,5R)-3,4-dibenzoyl-5-benzoylmethyltetrahydrofuran-2-yl)-3-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

2-(1-Methoxy-2-phenylethylidene)malononitrile

phenylacetyl chloride

5-Amino-3-benzyl-1H-pyrazole-4-carbonitrile

Downstream raw materials:

C₁₇H₂₂N₅O₁₃P₃

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