Acetic acid 2-(4-amino-5-cyano-pyrrolo(2,3-d)pyrimidin-7-ylmethoxy)ethyl ester

Base Information

• Chemical Name: Acetic acid 2-(4-amino-5-cyano-pyrrolo(2,3-d)pyrimidin-7-ylmethoxy)ethyl ester
• CAS No.: 120386-04-1
• Molecular Formula: C₁₂H₁₃N₅O₃
• Molecular Weight: 275.267
• ChEMBL ID: CHEMBL34633
• DSSTox Substance ID: DTXSID80923364
• Wikidata: Q82897374
• Mol file: 120386-04-1.mol

Synonyms:120386-04-1;2-((4-Amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methoxy)ethyl acetate;2-[(4-Amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl acetate;Acetic acid 2-(4-amino-5-cyano-pyrrolo(2,3-d)pyrimidin-7-ylmethoxy)ethyl ester;CHEMBL34633;DTXSID80923364;2-[(4-amino-5-cyano-pyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl acetate;Acetic acid 2-(4-amino-5-cyano-pyrrolo[2,3-d]pyrimidin-7-ylmethoxy)-ethyl ester

Chemical Property of Acetic acid 2-(4-amino-5-cyano-pyrrolo(2,3-d)pyrimidin-7-ylmethoxy)ethyl ester

Chemical Property:

• Vapor Pressure: 1.24E-11mmHg at 25°C
• Boiling Point: 537.7°Cat760mmHg
• Flash Point: 279°C
• Density: 1.43g/cm³
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 275.10183929
• Heavy Atom Count: 20
• Complexity: 396

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCCOCN1C=C(C2=C(N=CN=C21)N)C#N

Technology Process of Acetic acid 2-(4-amino-5-cyano-pyrrolo(2,3-d)pyrimidin-7-ylmethoxy)ethyl ester

There total 1 articles about Acetic acid 2-(4-amino-5-cyano-pyrrolo(2,3-d)pyrimidin-7-ylmethoxy)ethyl ester 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:

4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine (19393-83-0) + 2-acetoxyethoxymethyl bromide (81777-40-4) → 4-amino-5-cyano-7-<(2-acetoxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine (120386-04-1) + 4-amino-5-cyano-1-<(2-acetoxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine (120386-05-2)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jm00127a003

Reference yield: 7.0%

4-amino-5-cyano-7-<(2-acetoxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine (120386-04-1) → 2-amino-5-cyano-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine (120386-06-3) + 4-amino-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine-5-formimidate (120386-10-9)

Guidance literature:

With ammonia; at 5 ℃; for 6h;

DOI:10.1021/jm00127a003

Reference yield:

4-amino-5-cyano-7-<(2-acetoxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine (120386-04-1) → 4-amino-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine-5-carboxamide (120386-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / methanolic ammonia / 6 h / 5 °C

2: 56 percent / NH₄OH, 30percent H₂O₂ / H₂O / 1 h / Ambient temperature

With ammonium hydroxide; ammonia; dihydrogen peroxide; In water;

DOI:10.1021/jm00127a003

upstream raw materials:

4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine

2-acetoxyethoxymethyl bromide

Downstream raw materials:

2-amino-5-cyano-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine

4-amino-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine-5-formimidate

4-amino-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine-5-carboxamide

4-amino-7-<(2-hydroxyethoxy)methyl>pyrrolo<2,3-d>pyrimidine-5-thiocarboxamide

Refernces