Bicyclo[2.2.2]octane-1-propanoic acid, 4-[[[6-amino-1,2,3,4-tetrahydro-2,4-dioxo-3-propyl-1-(propyl-1,1,2,2,3,3,3-d7)-5-pyrimidinyl]amino]carbonyl]-,

Base Information

• Chemical Name: Bicyclo[2.2.2]octane-1-propanoic acid, 4-[[[6-amino-1,2,3,4-tetrahydro-2,4-dioxo-3-propyl-1-(propyl-1,1,2,2,3,3,3-d7)-5-pyrimidinyl]amino]carbonyl]-,
• CAS No.: 959958-69-1
• Molecular Formula: C₂₃H₃₆N₄O₅
• Molecular Weight: 455.507
• Mol file: 959958-69-1.mol

Synonyms:Bicyclo[2.2.2]octane-1-propanoic acid, 4-[[[6-amino-1,2,3,4-tetrahydro-2,4-dioxo-3-propyl-1-(propyl-1,1,2,2,3,3,3-d7)-5-pyrimidinyl]amino]carbonyl]-,

Chemical Property of Bicyclo[2.2.2]octane-1-propanoic acid, 4-[[[6-amino-1,2,3,4-tetrahydro-2,4-dioxo-3-propyl-1-(propyl-1,1,2,2,3,3,3-d7)-5-pyrimidinyl]amino]carbonyl]-,

Chemical Property:

• PSA: 125.42000
• LogP: 3.29870

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[2.2.2]octane-1-propanoic acid, 4-[[[6-amino-1,2,3,4-tetrahydro-2,4-dioxo-3-propyl-1-(propyl-1,1,2,2,3,3,3-d7)-5-pyrimidinyl]amino]carbonyl]-,

There total 9 articles about Bicyclo[2.2.2]octane-1-propanoic acid, 4-[[[6-amino-1,2,3,4-tetrahydro-2,4-dioxo-3-propyl-1-(propyl-1,1,2,2,3,3,3-d7)-5-pyrimidinyl]amino]carbonyl]-, 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: 77.0%

4-(2-methoxycarbonyl-ethyl)-bicyclo[2.2.2]octane-1-carboxylic acid (340023-15-6) + 5,6-diamino-1-heptadeuteriopropyl-3-propyl-1H-pyrimidine-2,4-dione hydrochloride → 3-(4-(6-amino-2,4-dioxo-1-propyl-3-heptadeuteriopropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[2.2.2]oct-1-yl)propionic acid methyl ester (959958-69-1)

Guidance literature:

With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1002/jlcr.1237

Reference yield:

4-formyl-bicyclo[2.2.2]octane-1-carboxylic acid (96102-85-1) → 3-(4-(6-amino-2,4-dioxo-1-propyl-3-heptadeuteriopropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[2.2.2]oct-1-yl)propionic acid methyl ester (959958-69-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / KHMDS / toluene; tetrahydrofuran / 16 h / 20 °C

2: 81 percent / H₂ / Pd/C / ethyl acetate / 16 h / 20 °C

3: 77 percent / Et₃N; HATU / acetonitrile / 16 h / 20 °C

With hydrogen; potassium hexamethylsilazane; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; toluene; acetonitrile; 1: Horner-Emmons-Wadsworth reaction;

DOI:10.1002/jlcr.1237

Reference yield:

4-(2-methoxycarbonyl-vinyl)-bicyclo[2.2.2]octane-1-carboxylic acid → 3-(4-(6-amino-2,4-dioxo-1-propyl-3-heptadeuteriopropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[2.2.2]oct-1-yl)propionic acid methyl ester (959958-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / H₂ / Pd/C / ethyl acetate / 16 h / 20 °C

2: 77 percent / Et₃N; HATU / acetonitrile / 16 h / 20 °C

With hydrogen; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In ethyl acetate; acetonitrile;

DOI:10.1002/jlcr.1237

upstream raw materials:

4-(2-methoxycarbonyl-ethyl)-bicyclo[2.2.2]octane-1-carboxylic acid

4-formyl-bicyclo[2.2.2]octane-1-carboxylic acid

(6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-carbamic acid tert-butyl ester

(6-amino-2,4-dioxo-1-heptadeuteriopropyl-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-carbamic acid tert-butyl ester

Refernces