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

Base Information

Chemical Name:diethyl N-{2-pivaloylamino-4-methyl[(pyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate
CAS No.:306314-98-7
Molecular Formula:C₃₀H₃₅N₅O₆
Molecular Weight:561.638
Hs Code.:

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

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

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

There total 9 articles about diethyl N-{2-pivaloylamino-4-methyl[(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: 42.7%

: 116387-21-4
4-iodobenzoyl-L-glutamic acid diethyl ester

: 306314-97-6
2-pivaloylamino-4-methyl-5-ethynylpyrrolo[2,3-d]pyrimidine

: 306314-98-7
diethyl N-{2-pivaloylamino-4-methyl[(pyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate

Guidance literature:: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 20 ℃; for 28h;
DOI:10.1021/jm000200l

Reference yield:

: 6940-45-0
5-(2-hydroxyethyl)-6-methyl-2-aminouracil

: 306314-98-7
diethyl N-{2-pivaloylamino-4-methyl[(pyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate

Guidance literature:: Multi-step reaction with 9 steps

1: 68 percent / POCl₃ / 2 h / 110 °C

2: 50 percent / Et₃N / butan-1-ol / 72 h / 110 °C

3: 45 percent / MnO₂ / dioxane / 24 h / 110 - 120 °C

4: 65 percent / Na; liq. NH₃ / 1.5 h / -78 °C

5: 65 percent / pyridine / 2 h / Heating

6: 52 percent / N-iodosuccinimide / tetrahydrofuran / 8 h / 20 °C

7: 45.5 percent / CuI; tetrakis(triphenylphosphine)palladium⁽⁰⁾; Et₃N / tetrahydrofuran / 20 °C

8: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 50 °C

9: 42.7 percent / CuI; tetrakis(triphenylphosphine)palladium⁽⁰⁾; Et₃N / tetrahydrofuran / 28 h / 20 °C

With pyridine; manganese(IV) oxide; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; ammonia; sodium; triethylamine; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; butan-1-ol; 1: Chlorination / 2: cyclocondensation / 3: Aromatization / 4: Reduction / 5: Acylation / 6: Iodination / 7: Substitution / 8: desilylation / 9: Arylation;
DOI:10.1021/jm000200l

Reference yield:

: 306314-93-2
4-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine

: 306314-98-7
diethyl N-{2-pivaloylamino-4-methyl[(pyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]benzoyl}-L-glutamate

Guidance literature:: Multi-step reaction with 5 steps

1: 65 percent / pyridine / 2 h / Heating

2: 52 percent / N-iodosuccinimide / tetrahydrofuran / 8 h / 20 °C

3: 45.5 percent / CuI; tetrakis(triphenylphosphine)palladium⁽⁰⁾; Et₃N / tetrahydrofuran / 20 °C

4: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 50 °C

5: 42.7 percent / CuI; tetrakis(triphenylphosphine)palladium⁽⁰⁾; Et₃N / tetrahydrofuran / 28 h / 20 °C

With pyridine; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 1: Acylation / 2: Iodination / 3: Substitution / 4: desilylation / 5: Arylation;
DOI:10.1021/jm000200l