4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl ester

Base Information

• Chemical Name: 4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl ester
• CAS No.: 111113-66-7
• Molecular Formula: C₂₂H₂₄N₄O₆
• Molecular Weight: 440.456
• Mol file: 111113-66-7.mol

Synonyms:4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl ester

Chemical Property of 4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl ester

There total 1 articles about 4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl 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:

4-{Acetyl-[3-oxo-4-(triphenyl-λ5-phosphanylidene)-butyl]-amino}-benzoic acid ethyl ester (111113-65-6) + 2-acetamido-4-hydroxy-6-formylpyrimidine (60656-63-5) → 4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl ester (111113-66-7)

Guidance literature:

With bis(trifluoromethylsilyl)trifluoroacetamide; Yield given. Multistep reaction; 1.) DMF, 1 h, 2.) 65 h;

DOI:10.1021/jm00396a022

Reference yield: 48.0%

4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl ester (111113-66-7) → 1-(2'-acetamido-4'-hydroxy-6'-pyrimidinyl)-5-(N-acetyl-p-carbethoxyanilino)pentan-3-one (111113-67-8)

Guidance literature:

With hydrogen; Rh on carbon; In N,N-dimethyl-formamide; for 125h;

DOI:10.1021/jm00396a022

Reference yield:

4-{Acetyl-[(E)-5-(2-acetylamino-6-hydroxy-pyrimidin-4-yl)-3-oxo-pent-4-enyl]-amino}-benzoic acid ethyl ester (111113-66-7) → 5,6,7,8-tetrahydro-8-deazahomofolic acid

Guidance literature:

Multi-step reaction with 8 steps

1: 48 percent / H₂ / Rh/C / dimethylformamide / 125 h

2: 1.) HCl, EtOH, 2.) Na₂CO₃, NaOH / 1.) reflux, 45 min, 2.) C₆H₆, pH 8, 0 deg C, 30 min

3: 78 percent / H₂ / Pd black / dimethylformamide / 30 h / 760 Torr

4: 46 percent / aq. NaOH / 2.5 h / 90 °C

5: 100 percent / 3 h / Heating

6: 1.) Et₃N, isobutyl chloroformate / 1.) DMF, 1 h, 2.) room temperature, 1 h

7: 100 percent / H₂, CF₃COOH / PtO₂ / ethanol / 20 h / 760 Torr

8: aq. NaOH / 3 h

With hydrogenchloride; sodium hydroxide; ethanol; hydrogen; sodium carbonate; triethylamine; trifluoroacetic acid; isobutyl chloroformate; platinum(IV) oxide; Rh on carbon; palladium; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00396a022

upstream raw materials:

4-{Acetyl-[3-oxo-4-(triphenyl-λ⁵-phosphanylidene)-butyl]-amino}-benzoic acid ethyl ester

2-acetamido-4-hydroxy-6-formylpyrimidine

Downstream raw materials:

1-(2'-acetamido-4'-hydroxy-6'-pyrimidinyl)-5-(N-acetyl-p-carbethoxyanilino)pentan-3-one

8-deazahomopteroic acid

ethyl N¹¹-acetyl-8-deazahomopteroate

4-[[2-(2-Amino-4-hydroxy-pyrido[3,2-d]pyrimidin-6-yl)-ethyl]-(2,2,2-trifluoro-acetyl)-amino]-benzoic acid