(S)-5,6-diphenyl-N-((tetrahydrofuran-2-yl)methyl)furo[2,3-d]pyrimidin-4-amine

Base Information

• Chemical Name: (S)-5,6-diphenyl-N-((tetrahydrofuran-2-yl)methyl)furo[2,3-d]pyrimidin-4-amine
• CAS No.: 873305-35-2
• Molecular Formula: C₂₃H₂₁N₃O₂
• Molecular Weight: 371.439
• ChEMBL ID: CHEMBL247070
• DSSTox Substance ID: DTXSID20467671
• Pharos Ligand ID: YD45ZT38BFGR
• Wikidata: Q82294715
• Mol file: 873305-35-2.mol

Synonyms:5,6-diphenyl-N-((2S)-tetrahydro-2-furanylmethyl)furo(2,3-d)pyrimidin-4-amine;AIM-100;furo(2,3-d)pyrimidin-4-amine, 5,6-diphenyl-N-(((2S)-tetrahydro-2-furanyl)methyl)-

Chemical Property of (S)-5,6-diphenyl-N-((tetrahydrofuran-2-yl)methyl)furo[2,3-d]pyrimidin-4-amine

Chemical Property:

• Boiling Point: 552.9±50.0 °C(Predicted)
• PKA: 4.62±0.40(Predicted)
• PSA: 60.18000
• Density: 1.243±0.06 g/cm3(Predicted)
• LogP: 5.22070
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: insoluble in H2O; ≥35.8 mg/mL in EtOH with gentle warming; ≥36 mg/mL in DMSO with gentle warming
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 371.16337692
• Heavy Atom Count: 28
• Complexity: 492

Purity/Quality:

97% ^*data from raw suppliers

AIM 100 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1)CNC2=C3C(=C(OC3=NC=N2)C4=CC=CC=C4)C5=CC=CC=C5
• Isomeric SMILES: C1C[C@H](OC1)CNC2=C3C(=C(OC3=NC=N2)C4=CC=CC=C4)C5=CC=CC=C5
• Uses: AIM-100 modulates ligand-independent AR activity and inhibits prostate cell growth.

Technology Process of (S)-5,6-diphenyl-N-((tetrahydrofuran-2-yl)methyl)furo[2,3-d]pyrimidin-4-amine

There total 6 articles about (S)-5,6-diphenyl-N-((tetrahydrofuran-2-yl)methyl)furo[2,3-d]pyrimidin-4-amine 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: 87.0%

4-chloro-5,6-diphenylfuro[2,3-d]pyrimidine (65148-07-4) + S-tetrahydrofurfurylamine (4795-29-3,7202-43-9,13346-01-5,7175-81-7) → 5,6-diphenyl-4-[(S)-(tetrahydrofuran-2-yl)-methyl]aminofuro[2,3-d]pyrimidine (873305-35-2)

Guidance literature:

In ethanol; for 5h; Reflux;

Reference yield:

4-bromo-5,6-diphenyl-furo[2,3-d]pyrimidine (873306-32-2) + S-tetrahydrofurfurylamine (4795-29-3,7202-43-9,13346-01-5,7175-81-7) → 5,6-diphenyl-4-[(S)-(tetrahydrofuran-2-yl)-methyl]aminofuro[2,3-d]pyrimidine (873305-35-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 120 ℃; for 1.5h;

Reference yield:

2-amino-3-cyano-4,5-diphenylfuran (5503-73-1) → 5,6-diphenyl-4-[(S)-(tetrahydrofuran-2-yl)-methyl]aminofuro[2,3-d]pyrimidine (873305-35-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic anhydride / 6 h / 60 °C

1.2: 12 h / 0 - 20 °C

2.1: acetic acid / 1 h / 200 °C / Microwave irradiation

3.1: trichlorophosphate / 2 h / 55 °C / Inert atmosphere

4.1: ethanol / 5 h / Reflux

With acetic anhydride; acetic acid; trichlorophosphate; In ethanol;

upstream raw materials:

4-bromo-5,6-diphenyl-furo[2,3-d]pyrimidine

S-tetrahydrofurfurylamine

4-chloro-5,6-diphenylfuro[2,3-d]pyrimidine

2-amino-3-cyano-4,5-diphenylfuran