diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate

Base Information

• Chemical Name: diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate
• CAS No.: 149765-17-3
• Molecular Formula: C₂₉H₃₂ClN₅O₆
• Molecular Weight: 582.056
• Mol file: 149765-17-3.mol

Synonyms:diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate

Chemical Property of diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate

There total 6 articles about diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate 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: 58.0%

diethyl N-(4-ethynylbenzoyl)-L-glutamate (116387-23-6) + N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-16-2) → diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate (149765-17-3)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; for 4h; Ambient temperature;

DOI:10.3987/COM-92-S(T)65

Reference yield:

N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-15-1) → diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate (149765-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodosuccinimide / dimethylformamide / 20 °C

2: Pd(PPh₃)4; CuI; NEt₃ / dimethylformamide

With N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; 2: Sonogashira coupling;

DOI:10.1021/jm0203534

Reference yield:

N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide (137281-08-4) → diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate (149765-17-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 41 percent / phosphorus oxychloride / 2 h / Heating

2: N-iodosuccinimide / dimethylformamide / 20 °C

3: Pd(PPh₃)4; CuI; NEt₃ / dimethylformamide

With N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; trichlorophosphate; In N,N-dimethyl-formamide; 3: Sonogashira coupling;

DOI:10.1021/jm0203534

upstream raw materials:

diethyl N-(4-ethynylbenzoyl)-L-glutamate

N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide

N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide

N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide

Downstream raw materials:

diethyl N-<2-pivaloylamino<(5,6-dihydropyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate

diethyl N-<2-pivaloylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate

diethyl N-<2-pivaloylamino-4-chloro<(pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate

diethyl N-<2-pivaloylamino-4-mercapto<(pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate