5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester

Base Information

• Chemical Name: 5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester
• CAS No.: 1052647-47-8
• Molecular Formula: C₂₈H₄₁N₅O₅S
• Molecular Weight: 559.73
• Mol file: 1052647-47-8.mol

Synonyms:5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester

Chemical Property of 5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester

There total 6 articles about 5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester 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: 71.0%

5-[2-amino-6-(2-carboxyethylsulfanyl)pyrimidin-4-yl]-2,4-dimethylbenzoic acid tert-butyl ester (1052647-40-1) + N-Boc-1,3-diaminopropane (75178-96-0) → 5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester (1052647-47-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 25 ℃; for 6h;

DOI:10.1016/j.bmcl.2011.11.100

Reference yield:

5-(2-amino-6-chloro-pyrimidin-4-yl)-2,4-dimethylbenzoic acid tert-butyl ester (1052647-13-8) → 5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester (1052647-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 20 - 25 °C

With benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.11.100

Reference yield:

5-iodo-2,4-dimethylbenzoic acid (742081-03-4) → 5-{2-amino-6-[2-(3-tert-butoxycarbonylamino-propylcarbamoyl)-ethylsulfanyl]-pyrimidin-4-yl}-2,4-dimethyl-benzoic acid tert-butyl ester (1052647-47-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene / 2 h / 80 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 18 h / 80 °C

3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydrogencarbonate / 1,4-dioxane; water / 0.17 h / 80 °C

3.2: 19 h / 80 °C

4.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 20 - 25 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium hydrogencarbonate; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2011.11.100

upstream raw materials:

5-[2-amino-6-(2-carboxyethylsulfanyl)pyrimidin-4-yl]-2,4-dimethylbenzoic acid tert-butyl ester

N-Boc-1,3-diaminopropane

5-iodo-2,4-dimethylbenzoic acid

5-iodo-2,4-dimethylbenzoic acid tert-butyl ester