diethyl N-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate

Base Information

• Chemical Name: diethyl N-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate
• CAS No.: 502160-41-0
• Molecular Formula: C₃₁H₃₇N₅O₆
• Molecular Weight: 575.665

Synonyms:diethyl N-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate

Chemical Property of diethyl N-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate

Chemical Property:

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Technology Process of diethyl N-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate

There total 7 articles about diethyl N-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[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: 24.0%

4-iodobenzoyl-L-glutamic acid diethyl ester (116387-21-4) + 2-pivaloylamino-4-ethyl-5-ethynylpyrrolo[2,3-d]pyrimidine (502160-45-4) → diethyl N-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate (502160-41-0)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 20 ℃; for 4h;

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-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate (502160-41-0)

Guidance literature:

Multi-step reaction with 7 steps

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

2: 70 percent / Pd(PPh₃)4 / toluene / 3 h / Heating

3: 91 percent / H₂ / 5percent Pd/C / tetrahydrofuran; CH₂Cl₂ / 18 h / 2585.81 Torr

4: 56 percent / N-iodosuccinimide / tetrahydrofuran / 1 h / 20 °C

5: 75 percent / Pd(PPh₃)4; CuI; NEt₃ / tetrahydrofuran; dimethylformamide / 4 h / 20 °C

6: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 50 °C

7: 24 percent / Pd(PPh₃)4; CuI; NEt₃ / tetrahydrofuran / 4 h / 20 °C

With N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; hydrogen; triethylamine; trichlorophosphate; 5percent Pd/C; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Stille coupling;

DOI:10.1021/jm0203534

Reference yield:

N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-15-1) → diethyl N-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate (502160-41-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / Pd(PPh₃)4 / toluene / 3 h / Heating

2: 91 percent / H₂ / 5percent Pd/C / tetrahydrofuran; CH₂Cl₂ / 18 h / 2585.81 Torr

3: 56 percent / N-iodosuccinimide / tetrahydrofuran / 1 h / 20 °C

4: 75 percent / Pd(PPh₃)4; CuI; NEt₃ / tetrahydrofuran; dimethylformamide / 4 h / 20 °C

5: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 50 °C

6: 24 percent / Pd(PPh₃)4; CuI; NEt₃ / tetrahydrofuran / 4 h / 20 °C

With N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; hydrogen; triethylamine; 5percent Pd/C; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Stille coupling;

DOI:10.1021/jm0203534

upstream raw materials:

4-iodobenzoyl-L-glutamic acid diethyl ester

2-pivaloylamino-4-ethyl-5-ethynylpyrrolo[2,3-d]pyrimidine

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-{4-[2-(2-pivaloylamino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate

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