4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• CAS No.: 186301-25-7
• Molecular Formula: C₂₀H₂₁IN₄O₃
• Molecular Weight: 492.316
• Mol file: 186301-25-7.mol

Synonyms:4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

Chemical Property of 4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

There total 4 articles about 4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 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: 78.5%

aniline (62-53-3) + 4-chloro-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (186394-15-0) → 4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (186301-25-7)

Guidance literature:

With sodium acetate; In ethanol; for 24h; Heating;

DOI:10.1021/jm0000259

Reference yield:

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (123148-78-7) → 4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (186301-25-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / acetonitrile / 16 h / Ambient temperature

2: NaOAc / ethanol

With sodium acetate; sodium hydride; In ethanol; acetonitrile;

DOI:10.1080/07328319708006124

Reference yield:

(3aR,6R,6aR)-2,2,6-trimethyltetrahydro-2H-furo(3,4-d)(1,3)dioxol-4-ol (158112-53-9) → 4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (186301-25-7)

Guidance literature:

Multi-step reaction with 3 steps

1: CCl₄ / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.75 h / -78 - -68 °C

2: NaH / acetonitrile / 16 h / Ambient temperature

3: NaOAc / ethanol

With tetrachloromethane; sodium acetate; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; acetonitrile;

DOI:10.1080/07328319708006124

upstream raw materials:

aniline

4-chloro-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

(3aR,6R,6aR)-2,2,6-trimethyltetrahydro-2H-furo(3,4-d)(1,3)dioxol-4-ol

Downstream raw materials:

4-N-phenylamino-5-phenyl-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

GP683

(2R,3R,4S,5R)-2-(5-Iodo-4-phenylamino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-methyl-tetrahydro-furan-3,4-diol