N-{2-[(cyclohexylcarbamoyl)amino]ethyl}-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)

Base Information

• Chemical Name: N-{2-[(cyclohexylcarbamoyl)amino]ethyl}-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)
• CAS No.: 75930-33-5
• Molecular Formula: C18H27 N5 O7
• Molecular Weight: 425.4363

Synonyms:NSC317316

Chemical Property of N-{2-[(cyclohexylcarbamoyl)amino]ethyl}-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.46g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-{2-[(cyclohexylcarbamoyl)amino]ethyl}-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)

There total 2 articles about N-{2-[(cyclohexylcarbamoyl)amino]ethyl}-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name) 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: 53.0%

N-(2-aminoethyl)-N-cyclohexylurea (75930-39-1) + 1-deoxy-1-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-β-D-ribofuranuronic acid (3415-07-4) → N-<2-(3-cyclohexylureido)ethyl>-1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-ribofuranuronamide (75930-33-5)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; 1.) -20 deg C, 1 h, 2.) 20 deg C, 20 h;

DOI:10.1021/jm00134a011

Reference yield:

Cyclohexyl isocyanate (3173-53-3) → N-<2-(3-cyclohexylureido)ethyl>-1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-ribofuranuronamide (75930-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / CHCl₃ / 2 h

2: 53 percent / triethylamine, diphenylphosphoryl azide / dimethylformamide / 1.) -20 deg C, 1 h, 2.) 20 deg C, 20 h

With diphenylphosphoranyl azide; triethylamine; In chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm00134a011

Reference yield: 38.0%

N-<2-(3-cyclohexylureido)ethyl>-1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-ribofuranuronamide (75930-33-5) → N-<2-(3-cyclohexyl-1-nitrosoureido)ethyl>-1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-ribofuranuronamide (75930-26-6)

Guidance literature:

With formic acid; sodium nitrite; for 0.5h;

DOI:10.1021/jm00134a011

upstream raw materials:

N-(2-aminoethyl)-N-cyclohexylurea

1-deoxy-1-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-β-D-ribofuranuronic acid

Cyclohexyl isocyanate

Downstream raw materials:

N-<2-(3-cyclohexyl-1-nitrosoureido)ethyl>-1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-ribofuranuronamide

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