4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid

Base Information

• Chemical Name: 4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid
• CAS No.: 173850-11-8
• Molecular Formula: C₁₅H₁₆N₄O₃
• Molecular Weight: 300.317
• Mol file: 173850-11-8.mol

Synonyms:4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid

Chemical Property of 4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid

There total 5 articles about 4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid 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: 93.0%

4-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-7-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethyl}-benzoic acid methyl ester (173850-10-7) → 4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid (173850-11-8)

Guidance literature:

With sulfuric acid; at 100 ℃; for 1.5h;

DOI:10.1021/jo951471k

Reference yield:

4-ethynylbenzoic acid methyl ester (3034-86-4) → 4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid (173850-11-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾, CuI, Et₃N / CH₂Cl₂ / 3 h / Heating

2: 94 percent / H₂ / 20percent Pd(OH)2/C / methanol; acetone / 12 h / 760 Torr

3: 93 percent / H₂SO₄ (conc) / 1.5 h / 100 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; hydrogen; triethylamine; palladium dihydroxide; In methanol; dichloromethane; acetone;

DOI:10.1021/jo951471k

Reference yield:

6-iodo-4(3H)-oxo-2-pivaloylamino-7H-pyrrolo<2,3-d>pyrimidine (143682-15-9) → 4-<2-(2-amino-4(3H)-oxo-5,6-dihydro-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoic acid (173850-11-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 54 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) room temperature

2: 85 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾, CuI, Et₃N / CH₂Cl₂ / 3 h / Heating

3: 94 percent / H₂ / 20percent Pd(OH)2/C / methanol; acetone / 12 h / 760 Torr

4: 93 percent / H₂SO₄ (conc) / 1.5 h / 100 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; hydrogen; sodium hydride; triethylamine; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo951471k

upstream raw materials:

4-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-7-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethyl}-benzoic acid methyl ester

4-ethynylbenzoic acid methyl ester

6-iodo-4(3H)-oxo-2-pivaloylamino-7H-pyrrolo<2,3-d>pyrimidine

2-(pivaloylamino)-4(3H)-oxo-6-iodo-7-tosyl-7H-pyrrolo<2,3-d>pyrimidine