tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate

Base Information

• Chemical Name: tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate
• CAS No.: 149325-63-3
• Molecular Formula: C₂₀H₂₅N₃O₃
• Molecular Weight: 355.437
• Mol file: 149325-63-3.mol

Synonyms:tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate

Chemical Property of tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate

There total 6 articles about tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate 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: 66.0%

guanidine hydrochloride (50-01-1) + tert-butyl 4-<2-<2-(methoxycarbonyl)-3-oxocyclopentanyl>ethyl>benzoate (149325-62-2) → tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate (149325-63-3)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; Heating;

DOI:10.1021/jm00037a012

Reference yield:

4-(tert-butoxycarbonyl)benzaldehyde (65874-27-3) → tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate (149325-63-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-butyllithium / 1.) THF, hexane, 1 h, 2.) hexane, THF, 30 min

2: 1.) 9-BBN, 2.) aq. 6N NaOH, H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, H₂O, RT, 1 h

3: triethylamine / CH₂Cl₂

4: NaI / acetone / Heating

5: tributyltin hydride, AIBN / benzene / Heating

6: 66 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / Heating

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine; sodium iodide; In dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jm00037a012

Reference yield:

4-t-butyloxycarbonylstyrene (84740-98-7) → tert-butyl 4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoate (149325-63-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 9-BBN, 2.) aq. 6N NaOH, H₂O₂ / 1.) THF, RT, 2 h, 2.) THF, H₂O, RT, 1 h

2: triethylamine / CH₂Cl₂

3: NaI / acetone / Heating

4: tributyltin hydride, AIBN / benzene / Heating

5: 66 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / Heating

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine; sodium iodide; In dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jm00037a012

upstream raw materials:

guanidine hydrochloride

tert-butyl 4-<2-<2-(methoxycarbonyl)-3-oxocyclopentanyl>ethyl>benzoate

4-(tert-butoxycarbonyl)benzaldehyde

4-t-butyloxycarbonylstyrene

Downstream raw materials:

(S)-2-{4-[2-(2-Amino-4-hydroxy-6,7-dihydro-5H-cyclopentapyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester

4-<2-(2-amino-6,7-dihydro-4-oxo-5H-cyclopentapyrimidin-5-yl)ethyl>benzoic acid