diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamate

Base Information

Chemical Name:diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamate
CAS No.:150586-00-8
Molecular Formula:C₂₅H₃₁N₅O₆
Molecular Weight:497.551
Hs Code.:

Synonyms:diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamate

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Chemical Property of diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamate

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Technology Process of diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamate

There total 8 articles about diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]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:

: 1118-89-4
diethyl-L-glutamate hydrochloride

: 4-[1-(2-amino-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-propyl]-benzoic acid

: 150586-00-8
diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamate

Guidance literature:: With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1248/cpb.49.1280

Reference yield:

: 65874-27-3
4-(tert-butoxycarbonyl)benzaldehyde

: 150586-00-8
diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 79 percent / toluene / 2 h / Heating

2.1: PhSCu / tetrahydrofuran / -40 - -15 °C

2.2: 32 percent / tetrahydrofuran / 1 h / 0 °C

3.1: 88 percent / LiBH₄ / diethyl ether / 13 h / 20 °C

4.1: 91 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

5.1: 89 percent / 5,5-dibromobarbituric acid / diethyl ether / 64 h / 20 °C

6.1: 45 percent / K₂CO₃ / dimethylsulfoxide / 4 h / 20 °C

7.1: trifluoroacetic acid / CH₂Cl₂ / 4 h / 20 °C

8.1: diethyl cyanophosphonate; Et₃N / dimethylformamide / 18 h / 20 °C

With lithium borohydride; oxalyl dichloride; 5,5-dibromobarbituric acid; diethyl cyanophosphonate; copper(I) thiophenolate; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 4.1: Swern oxidation;
DOI:10.1248/cpb.49.1280

Reference yield:

: 146943-27-3
methyl 3-<4-(tert-butoxycarbonyl)phenyl>propenoate

: 150586-00-8
diethyl N-{4-[1-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamate

Guidance literature:: Multi-step reaction with 7 steps

1.1: PhSCu / tetrahydrofuran / -40 - -15 °C

1.2: 32 percent / tetrahydrofuran / 1 h / 0 °C

2.1: 88 percent / LiBH₄ / diethyl ether / 13 h / 20 °C

3.1: 91 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

4.1: 89 percent / 5,5-dibromobarbituric acid / diethyl ether / 64 h / 20 °C

5.1: 45 percent / K₂CO₃ / dimethylsulfoxide / 4 h / 20 °C

6.1: trifluoroacetic acid / CH₂Cl₂ / 4 h / 20 °C

7.1: diethyl cyanophosphonate; Et₃N / dimethylformamide / 18 h / 20 °C

With lithium borohydride; oxalyl dichloride; 5,5-dibromobarbituric acid; diethyl cyanophosphonate; copper(I) thiophenolate; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.1248/cpb.49.1280