diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate

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Chemical Name:diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate
CAS No.:125991-54-0
Molecular Formula:C₂₅H₃₁N₅O₆
Molecular Weight:497.551
Hs Code.:

Synonyms:diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate

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Chemical Property of diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate

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Technology Process of diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate

There total 21 articles about diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-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: 51.0%

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

: 144051-63-8
4-[3-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoic acid

: 125991-54-0
diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate

Guidance literature:: 4-[3-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoic acid; With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

diethyl-L-glutamate hydrochloride; With 4-methyl-morpholine; In N,N-dimethyl-formamide; at 20 ℃; for 3.5h;
DOI:10.1021/jo030248h

Reference yield:

: 123910-86-1
4-(4-hydroxybut-1-ynyl)benzoic acid methyl ester

: 125991-54-0
diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / H₂ / Pd/C / ethanol / 18 h / 2585.74 Torr

2.1: 90 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 3 h / 20 °C

3.1: 61 percent / aq. NaOH / ethanol / 48 h / 38 °C

4.1: 96 percent / CH₃SO₂Cl; Et₃N / CH₂Cl₂ / 0 - 20 °C

5.1: 85 percent / H₂O; ethyl acetate / 24 h / 50 °C

6.1: aq. NaOH / 2 h / 20 °C

6.2: aq. H₂SO₄ / 3 h / 0 °C

6.3: 50.7 percent / aq. NaOH / 1 h / 20 °C / pH 7

7.1: 4-methylmorpholine; 2-chloro-4,6-dimethoxy-1,3,5-triazine / dimethylformamide / 2 h / 20 °C

7.2: 51 percent / 4-methylmorpholine / dimethylformamide / 3.5 h / 20 °C

With 4-methyl-morpholine; sodium hydroxide; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; hydrogen; sodium acetate; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 3.1: Henry reaction / 5.1: Michael addition / 6.2: Nef reaction;
DOI:10.1021/jo030248h

Reference yield:

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

: 125991-54-0
diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate

Guidance literature:: Multi-step reaction with 8 steps

1: 1) NaH / 1) THF, reflux, 4 h, 2) THF, reflux, 1.5 h

2: 100 percent / H₂ / 10percent Pd/C / methanol / 4 h

3: 86 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -60 °C

4: 1) t-BuOK / 1) THF, toluene, 2) toluene, 0 deg C

5: 1) CH₂Cl₂, molecular sieves 3A, UV, 0 - 5 deg C, 2 h, 2) 10 min

6: 80 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating

7: CF₃COOH, H₂O

8: diethyl phosphorocyanidate, triethylamine / dimethylformamide

With oxalyl dichloride; diethyl cyanophosphonate; potassium tert-butylate; water; hydrogen; sodium hydride; potassium n-butoxide; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo00059a016