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

Base Information

• Chemical Name: diethyl N-<2-pivaloylamino-4-benzylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate
• CAS No.: 152169-91-0
• Molecular Formula: C₃₆H₄₀N₆O₆
• Molecular Weight: 652.75

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

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

Chemical Property:

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

There total 8 articles about diethyl N-<2-pivaloylamino-4-benzylamino<(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: 61.0%

4-iodobenzoyl-L-glutamic acid diethyl ester (116387-21-4) + 2-pivaloylamino-4-benzylamino-5-ethynylpyrrolo<2,3-d>pyrimidine (152169-90-9) → diethyl N-<2-pivaloylamino-4-benzylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate (152169-91-0)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

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

Reference yield:

pivaloyl chloride (3282-30-2) → diethyl N-<2-pivaloylamino-4-benzylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate (152169-91-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / pyridine / 0.5 h / Ambient temperature

2: 83 percent / N-iodosuccinimide / tetrahydrofuran / 1 h / Ambient temperature

3: 54 percent / copper(I) iodide, tetrakis(triphenylphosphine)palladium⁽⁰⁾, triethylamine / dimethylformamide / 18 h / Ambient temperature

4: 79 percent / 2-methoxy-ethanol / 1.5 h / 100 °C

5: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

6: 61 percent / copper(I) iodide, tetrakis(triphenylphosphine)palladium⁽⁰⁾, triethylamine / dimethylformamide / 1.5 h / Ambient temperature

With pyridine; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 2-methoxy-ethanol; N,N-dimethyl-formamide;

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

Reference yield:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → diethyl N-<2-pivaloylamino-4-benzylamino<(pyrrolo<2,3-d>pyrimidin-5-yl)ethynyl>benzoyl>-L-glutamate (152169-91-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / pyridine / 0.5 h / Ambient temperature

2: 83 percent / N-iodosuccinimide / tetrahydrofuran / 1 h / Ambient temperature

3: 54 percent / copper(I) iodide, tetrakis(triphenylphosphine)palladium⁽⁰⁾, triethylamine / dimethylformamide / 18 h / Ambient temperature

4: 79 percent / 2-methoxy-ethanol / 1.5 h / 100 °C

5: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

6: 61 percent / copper(I) iodide, tetrakis(triphenylphosphine)palladium⁽⁰⁾, triethylamine / dimethylformamide / 1.5 h / Ambient temperature

With pyridine; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 2-methoxy-ethanol; N,N-dimethyl-formamide;

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

upstream raw materials:

4-iodobenzoyl-L-glutamic acid diethyl ester

2-pivaloylamino-4-benzylamino-5-ethynylpyrrolo<2,3-d>pyrimidine

pivaloyl chloride

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Downstream raw materials:

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

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