diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate

Base Information

• Chemical Name: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate
• CAS No.: 243636-76-2
• Molecular Formula: C₃₂H₃₇N₅O₇
• Molecular Weight: 603.675

Synonyms:diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate

Chemical Property of diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate

Chemical Property:

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Technology Process of diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate

There total 12 articles about diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]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%

2-amino-4-oxo-5-vinyl-7-(4'-methoxybenzyl)-3,4,5,6-tetrahydropyrrolo[2,3-d]pyrimidine (348620-53-1) + 2-(4-iodo-benzoylamino)-pentanedioic acid diethyl ester → diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate (243636-76-2)

Guidance literature:

With copper(l) iodide; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In N,N-dimethyl-formamide;

DOI:10.1021/jo001580l

Reference yield:

methyl N-(4'-methoxybenzyl)carbamate (99075-91-9) → diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate (243636-76-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 20 °C

2.1: 88 percent / KOH; N₂H₄*H₂O / ethane-1,2-diol / 110 °C

3.1: 82 percent / Et₃N; DMAP / ethyl acetate / 0 - 20 °C

4.1: 92 percent / Mn(OAc)3*2H₂O; Cu(OAc)2*H₂O / acetic acid / 20 °C

5.1: 64 percent / P₄S₁₀ / tetrahydrofuran / Heating

6.1: NaOMe / methanol / 0.5 h / 20 °C

6.2: 72 percent / methanol / 1 h / 90 °C / 15 Torr

7.1: 61 percent / Et₃N; CuI; (o-tolyl)3P / Pd(OAc)2 / dimethylformamide

With dmap; potassium hydroxide; copper(l) iodide; tetraphosphorus decasulfide; copper diacetate; sodium methylate; manganese triacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; hydrazine hydrate; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In tetrahydrofuran; methanol; ethylene glycol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; 7.1: Heck reaction;

DOI:10.1021/jo001580l

Reference yield:

4-methoxy-benzylamine (2393-23-9) → diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate (243636-76-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 94 percent / K₂CO₃ / acetone / Heating

2.1: 99 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 20 °C

3.1: 88 percent / KOH; N₂H₄*H₂O / ethane-1,2-diol / 110 °C

4.1: 82 percent / Et₃N; DMAP / ethyl acetate / 0 - 20 °C

5.1: 92 percent / Mn(OAc)3*2H₂O; Cu(OAc)2*H₂O / acetic acid / 20 °C

6.1: 64 percent / P₄S₁₀ / tetrahydrofuran / Heating

7.1: NaOMe / methanol / 0.5 h / 20 °C

7.2: 72 percent / methanol / 1 h / 90 °C / 15 Torr

8.1: 61 percent / Et₃N; CuI; (o-tolyl)3P / Pd(OAc)2 / dimethylformamide

With dmap; potassium hydroxide; copper(l) iodide; tetraphosphorus decasulfide; copper diacetate; sodium methylate; manganese triacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; hydrazine hydrate; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In tetrahydrofuran; methanol; ethylene glycol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone; 8.1: Heck reaction;

DOI:10.1021/jo001580l

upstream raw materials:

4-iodobenzoyl-L-glutamic acid diethyl ester

2-amino-4-oxo-5-vinyl-7-(4'-methoxybenzyl)-3,4,5,6-tetrahydropyrrolo[2,3-d]pyrimidine

methyl N-(4'-methoxybenzyl)carbamate

4-methoxy-benzylamine

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