4-Amino-7-(4-hydroxy-5-hydroxymethyl-3-iodo-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carboxylic acid amide

Base Information

• Chemical Name: 4-Amino-7-(4-hydroxy-5-hydroxymethyl-3-iodo-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carboxylic acid amide
• CAS No.: 127880-97-1
• Molecular Formula: C₁₂H₁₄IN₅O₄
• Molecular Weight: 419.179
• DSSTox Substance ID: DTXSID60926015
• Wikidata: Q82900473
• ChEMBL ID: CHEMBL3142823
• Mol file: 127880-97-1.mol

Synonyms:127880-97-1;4-Amino-7-((2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-iodotetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide;4-Amino-7-(4-hydroxy-5-hydroxymethyl-3-iodo-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carboxylic acid amide;4-Amino-7-(4-hydroxy-5-hydroxymethyl-3-iodo-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid amide;CHEMBL3142823;DTXSID60926015;4-Amino-7-(2-deoxy-2-iodopentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboximidic acid;4-amino-7-[(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-iodo-tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide

Chemical Property of 4-Amino-7-(4-hydroxy-5-hydroxymethyl-3-iodo-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carboxylic acid amide

Chemical Property:

• Vapor Pressure: 6.18E-28mmHg at 25°C
• Boiling Point: 813°C at 760 mmHg
• Flash Point: 445.5°C
• Density: 2.46g/cm³
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 419.00905
• Heavy Atom Count: 22
• Complexity: 444

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

Technology Process of 4-Amino-7-(4-hydroxy-5-hydroxymethyl-3-iodo-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carboxylic acid amide

There total 4 articles about 4-Amino-7-(4-hydroxy-5-hydroxymethyl-3-iodo-tetrahydro-furan-2-yl)-7H-pyrrolo(2,3-d)pyrimidine-5-carboxylic acid amide 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: 52.0%

4-amino-5-cyano-7-(2-deoxy-2-iodo-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine (127880-96-0) → 4-amino-7-(2-deoxy-2-iodo-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carboxamide (127880-97-1)

Guidance literature:

With ammonium hydroxide; dihydrogen peroxide; 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-7-(2-deoxy-2-iodo-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carboxamide (127880-97-1)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 41 percent / sodium iodide / hexamethylphosphoric acid triamide / 12 h / Ambient temperature

3: 24 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

4: 52 percent / aq. ammonium hydroxide, 30percent aq. hydrogen peroxide / methanol / 3 h

With dmap; ammonium hydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium iodide; 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-iodo-β-D-arabinofuranosyl>pyrrolo<2,3-d>pyrimidine (127880-95-9) → 4-amino-7-(2-deoxy-2-iodo-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carboxamide (127880-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

2: 52 percent / aq. ammonium hydroxide, 30percent aq. hydrogen peroxide / methanol / 3 h

With ammonium hydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; In tetrahydrofuran; methanol;

DOI:10.1021/jm00174a011

upstream raw materials:

4-amino-5-cyano-7-(2-deoxy-2-iodo-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-iodo-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>-2-O-<(trifluoromethyl)sulfonyl>-β-D-ribofuranosyl>pyrrolo<2,3-d>pyrimidine