N-(4-(3-(2,4-Diamino-7H-pyrrolo(2,3-d)pyrimidin-5-yl)propyl)benzoyl)glutamic acid

Base Information

• Chemical Name: N-(4-(3-(2,4-Diamino-7H-pyrrolo(2,3-d)pyrimidin-5-yl)propyl)benzoyl)glutamic acid
• CAS No.: 125991-51-7
• Molecular Formula: C21H24 N6 O5
• Molecular Weight: 440.459
• UNII: 48GO5ZA420
• DSSTox Substance ID: DTXSID30155032
• Nikkaji Number: J373.867A
• Mol file: 125991-51-7.mol

Synonyms:N-(4-(3-(2,4-diamino-7H-pyrrolo(2,3-d)pyrimidin-5-yl)propyl)benzoyl)glutamic acid;TNP 351;TNP-351

Chemical Property of N-(4-(3-(2,4-Diamino-7H-pyrrolo(2,3-d)pyrimidin-5-yl)propyl)benzoyl)glutamic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 198.04000
• Density: 1.473g/cm³
• LogP: 2.24760
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 440.18081789
• Heavy Atom Count: 32
• Complexity: 671

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCCC2=CNC3=NC(=NC(=C23)N)N)C(=O)NC(CCC(=O)O)C(=O)O
• Isomeric SMILES: C1=CC(=CC=C1CCCC2=CNC3=NC(=NC(=C23)N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O

Technology Process of N-(4-(3-(2,4-Diamino-7H-pyrrolo(2,3-d)pyrimidin-5-yl)propyl)benzoyl)glutamic acid

There total 20 articles about N-(4-(3-(2,4-Diamino-7H-pyrrolo(2,3-d)pyrimidin-5-yl)propyl)benzoyl)glutamic acid 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: 91.0%

diethyl N-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]-pyrimidin-5-yl)propyl]benzoyl]-L-glutamate (125991-50-6) → N-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidine-5-yl)propyl]benzoyl]-L-glutamic acid (125991-51-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo00059a016

Reference yield:

4-(tert-butoxycarbonyl)benzaldehyde (65874-27-3) → N-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidine-5-yl)propyl]benzoyl]-L-glutamic acid (125991-51-7)

Guidance literature:

Multi-step reaction with 9 steps

1: t-BuOK / 2-methyl-propan-2-ol; diethyl ether / 2 h / 12 °C

2: 1.) H₂, 2.) 4-(N,N-dimethylamino)pyridine (DMAP), dicyclohexylcarbodiimide (DCC) / 1.) 5percent Pd/C / 1.) AcOEt, 4 at, 3 h, 2.) EtOH-CH₂Cl₂, 20 deg C, 18 h

3: 1.) LDA, 2.) I₂ / 1.) hexane, THF, -78 deg C, 10 min, 2.) a) -78 deg C, 20 min, b) from -78 deg C to 0 deg C, 30 min

4: 1.) NaH / 1.) Me₂SO, RT, 5 min, 2.) 20 deg C, 1 h

5: 89 percent / t-BuOK / 2-methyl-propan-2-ol / 4 h / Heating

6: 45 percent / BH₃-THF / 5 h / 0 °C

7: CF₃COOH / 2 h

8: diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 30 min, 2.) RT, 63 h

9: 89 percent / aq. NaOH / tetrahydrofuran / 2 h / 20 °C

With dmap; sodium hydroxide; borane-THF; diphenyl phosphoryl azide; potassium tert-butylate; hydrogen; iodine; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00106a012

Reference yield:

4-((1E,3E)-4-Ethoxycarbonyl-buta-1,3-dienyl)-benzoic acid tert-butyl ester (130351-29-0) → N-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidine-5-yl)propyl]benzoyl]-L-glutamic acid (125991-51-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) H₂, 2.) 4-(N,N-dimethylamino)pyridine (DMAP), dicyclohexylcarbodiimide (DCC) / 1.) 5percent Pd/C / 1.) AcOEt, 4 at, 3 h, 2.) EtOH-CH₂Cl₂, 20 deg C, 18 h

2: 1.) LDA, 2.) I₂ / 1.) hexane, THF, -78 deg C, 10 min, 2.) a) -78 deg C, 20 min, b) from -78 deg C to 0 deg C, 30 min

3: 1.) NaH / 1.) Me₂SO, RT, 5 min, 2.) 20 deg C, 1 h

4: 89 percent / t-BuOK / 2-methyl-propan-2-ol / 4 h / Heating

5: 45 percent / BH₃-THF / 5 h / 0 °C

6: CF₃COOH / 2 h

7: diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 30 min, 2.) RT, 63 h

8: 89 percent / aq. NaOH / tetrahydrofuran / 2 h / 20 °C

With dmap; sodium hydroxide; borane-THF; diphenyl phosphoryl azide; potassium tert-butylate; hydrogen; iodine; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00106a012

upstream raw materials:

diethyl N-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]-pyrimidin-5-yl)propyl]benzoyl]-L-glutamate

diethyl-L-glutamate hydrochloride

4-<2-(2,4-diamino-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoic acid

4-(4-carbomethoxyphenyl)butanal

Refernces

• 1、 Taylor, Edward C.,Mao, Zhenmin. "A ring-transformation/ring-annulation strategy for the synthesis of the DHFR inhibitor, TNP-351: A correction". . p. 7973 - 7974. Retrieved 2007/10/03.
• 2、 -. "Process for the preparation of pyrrolo[2,3-d]pyrimidines". . . Retrieved 2008/06/13.