4-Amino-7-(3-amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile

Base Information

• Chemical Name: 4-Amino-7-(3-amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile
• CAS No.: 127880-86-8
• Molecular Formula: C₁₂H₁₄N₆O₃
• Molecular Weight: 290.282
• DSSTox Substance ID: DTXSID50926009
• Nikkaji Number: J723.024I
• Wikidata: Q82900463
• ChEMBL ID: CHEMBL3142825
• Mol file: 127880-86-8.mol

Synonyms:127880-86-8;4-Amino-7-((2R,3S,4S,5R)-3-amino-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile;4-Amino-7-(3-amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile;4-Amino-7-(3-amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile;CHEMBL3142825;DTXSID50926009;4-Amino-7-(2-amino-2-deoxypentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile;4-Amino-7-(2-amino-2-deoxy-beta-D-arabino-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile;4-amino-7-[(2R,3S,4S,5R)-3-amino-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Chemical Property of 4-Amino-7-(3-amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile

Chemical Property:

• Vapor Pressure: 8.83E-21mmHg at 25°C
• Boiling Point: 703.6°C at 760 mmHg
• Flash Point: 379.3°C
• Density: 1.91g/cm³
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 290.11273833
• Heavy Atom Count: 21
• Complexity: 442

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)N)N)C#N
• Isomeric SMILES: C1=C(C2=C(N=CN=C2N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)N)N)C#N

Technology Process of 4-Amino-7-(3-amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile

There total 3 articles about 4-Amino-7-(3-amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile 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: 56.0%

4-amino-5-cyano-7-(2-deoxy-2-azido-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine (127880-85-7) → 4-amino-5-cyano-7-(2-deoxy-2-amino-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine (127880-86-8)

Guidance literature:

With 1.3-propanedithiol; triethylamine; In methanol; for 3h;

DOI:10.1021/jm00174a011

Reference yield:

4-amino-5-cyano-7-<3,5-O-<1,1,3,3-tetrakis(methylethyl)disiloxan-1,3-diyl>-β-D-ribofuranosyl>pyrrolo<2,3-d>pyrimidine (85335-79-1) → 4-amino-5-cyano-7-(2-deoxy-2-amino-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine (127880-86-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / 4-(dimethylamino)pyridine (4-DMAP) / 1,2-dichloro-ethane / 0 °C

2: 78 percent / lithium azide / hexamethylphosphoric acid triamide / 4 h / Ambient temperature

3: 60 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

4: 56 percent / 1,3-propanedithiol, triethylamine / methanol / 3 h

With 1.3-propanedithiol; dmap; lithium azide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dichloro-ethane;

DOI:10.1021/jm00174a011

Reference yield:

4-amino-5-cyano-7-<3,5-O-<1,1,3,3-tetrakis(methylethyl)disiloxan-1,3-diyl>-2-deoxy-2-azido-β-D-arabinofuranosyl>pyrrolo<2,3-d>pyrimidine (127880-84-6) → 4-amino-5-cyano-7-(2-deoxy-2-amino-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine (127880-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

2: 56 percent / 1,3-propanedithiol, triethylamine / methanol / 3 h

With 1.3-propanedithiol; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1021/jm00174a011

upstream raw materials:

4-amino-5-cyano-7-(2-deoxy-2-azido-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine

4-amino-5-cyano-7-<3,5-O-<1,1,3,3-tetrakis(methylethyl)disiloxan-1,3-diyl>-β-D-ribofuranosyl>pyrrolo<2,3-d>pyrimidine

4-amino-5-cyano-7-<3,5-O-<1,1,3,3-tetrakis(methylethyl)disiloxan-1,3-diyl>-2-deoxy-2-azido-β-D-arabinofuranosyl>pyrrolo<2,3-d>pyrimidine