di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]benzoyl}-L-glutamate

Base Information

• Chemical Name: di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]benzoyl}-L-glutamate
• CAS No.: 289677-67-4
• Molecular Formula: C₃₀H₃₈N₆O₆S
• Molecular Weight: 610.734

Synonyms:di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]benzoyl}-L-glutamate

Chemical Property of di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]benzoyl}-L-glutamate

Chemical Property:

Purity/Quality:

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Technology Process of di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]benzoyl}-L-glutamate

There total 9 articles about di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]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: 36.0%

L-glutamic acid di-tert-butyl ester hydrochloride (32677-01-3) + 4-[5-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-ylsulfanylmethyl)-pyridin-3-yl]-benzoic acid (289677-66-3) → di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]benzoyl}-L-glutamate (289677-67-4)

Guidance literature:

With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

DOI:10.1016/S0968-0896(00)00051-1

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) → di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]benzoyl}-L-glutamate (289677-67-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diboron pinacol ester; KOAc; PdCl₂(dppf) / dimethylformamide / 2 h / 80 °C

1.2: 54 percent / PdCl₂(dppf); aq. Na₂CO₃ / dimethylformamide / 12 h / 80 °C

2.1: 90 percent / Bu₄NF / tetrahydrofuran / 3 h / 25 °C

3.1: 92 percent / SOCl₂ / CH₂Cl₂ / 3 h / 50 °C

4.1: 87 percent / acetone / 0.5 h / Heating

5.1: 93 percent / aq. HCl / ethanol / 2 h / 40 °C

6.1: 94 percent / dimethylformamide / 2 h / 80 °C

7.1: 91 percent / LiOH; H₂O / methanol / 12 h / 25 °C

8.1: 36 percent / NaHCO₃; EDCI / dimethylformamide / 12 h / 25 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; thionyl chloride; tetrabutyl ammonium fluoride; water; potassium acetate; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; bis(pinacol)diborane; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Substitution / 1.2: Condensation / 2.1: silyl ether cleavage / 3.1: Chlorination / 4.1: Substitution / 5.1: Hydrolysis / 6.1: Substitution / 7.1: Hydrolysis / 8.1: Acylation;

DOI:10.1016/S0968-0896(00)00051-1

Reference yield:

3-bromo-5-(tert-butyldimethylsilanyloxymethyl)pyridine (152351-91-2) → di-tert-butyl N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)thiomethyl]-3-pyridinyl]benzoyl}-L-glutamate (289677-67-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diboron pinacol ester; KOAc; PdCl₂(dppf) / dimethylformamide / 2 h / 80 °C

1.2: 54 percent / PdCl₂(dppf); aq. Na₂CO₃ / dimethylformamide / 12 h / 80 °C

2.1: 90 percent / Bu₄NF / tetrahydrofuran / 3 h / 25 °C

3.1: 92 percent / SOCl₂ / CH₂Cl₂ / 3 h / 50 °C

4.1: 87 percent / acetone / 0.5 h / Heating

5.1: 93 percent / aq. HCl / ethanol / 2 h / 40 °C

6.1: 94 percent / dimethylformamide / 2 h / 80 °C

7.1: 91 percent / LiOH; H₂O / methanol / 12 h / 25 °C

8.1: 36 percent / NaHCO₃; EDCI / dimethylformamide / 12 h / 25 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; thionyl chloride; tetrabutyl ammonium fluoride; water; potassium acetate; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; bis(pinacol)diborane; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Substitution / 1.2: Condensation / 2.1: silyl ether cleavage / 3.1: Chlorination / 4.1: Substitution / 5.1: Hydrolysis / 6.1: Substitution / 7.1: Hydrolysis / 8.1: Acylation;

DOI:10.1016/S0968-0896(00)00051-1

upstream raw materials:

L-glutamic acid di-tert-butyl ester hydrochloride

4-[5-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-ylsulfanylmethyl)-pyridin-3-yl]-benzoic acid

4-methoxycarbonylphenyl bromide

3-bromo-5-(tert-butyldimethylsilanyloxymethyl)pyridine

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