4-(4-((1-phenylethyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-6-yl)-phenol, R-

Base Information

• Chemical Name: 4-(4-((1-phenylethyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-6-yl)-phenol, R-
• CAS No.: 187724-61-4
• Molecular Formula: C20H18N4O
• Molecular Weight: 330.389
• European Community (EC) Number: 808-564-7
• UNII: 9RIE5HW38P
• DSSTox Substance ID: DTXSID801346629
• Wikidata: Q27088404
• NCI Thesaurus Code: C1871
• Pharos Ligand ID: HHZPSBHNRB6Y
• ChEMBL ID: CHEMBL1963502
• Mol file: 187724-61-4.mol

Synonyms:4-(4-((1-phenylethyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-6-yl)-phenol, R-;4-phenethylamino-6-(yderoxyl)phenyl-7H-pyrrolo(2,3-d)pyrimidine;CGP 75166;CGP-75166;CGP75166;PKI 166;PKI-166;PKI166

Chemical Property of 4-(4-((1-phenylethyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-6-yl)-phenol, R-

Chemical Property:

• PSA: 73.83000
• LogP: 4.57660
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 330.14806121
• Heavy Atom Count: 25
• Complexity: 420

Purity/Quality:

≥98% ^*data from raw suppliers

PKI-166 ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NC2=NC=NC3=C2C=C(N3)C4=CC=C(C=C4)O
• Isomeric SMILES: C[C@H](C1=CC=CC=C1)NC2=NC=NC3=C2C=C(N3)C4=CC=C(C=C4)O

Technology Process of 4-(4-((1-phenylethyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-6-yl)-phenol, R-

There total 3 articles about 4-(4-((1-phenylethyl)amino)-7H-pyrrolo(2,3-d)pyrimidin-6-yl)-phenol, R- 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: 51.0%

(R)-6-(4-methoxyphenyl)-N-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine → 4-[4-[[(1R)-1-phenylethyl]amino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl]phenol (187724-61-4)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 6h;

Reference yield:

4-chloro-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (173459-03-5) + (R)-1-phenyl-ethyl-amine (3886-69-9) → 4-[4-[[(1R)-1-phenylethyl]amino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl]phenol (187724-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1: butan-1-ol / 145 °C

2: boron tribromide

With boron tribromide; In butan-1-ol;

DOI:10.1016/j.ejps.2014.04.011

Reference yield:

→ 4-[4-[[(1R)-1-phenylethyl]amino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl]phenol (187724-61-4)

Guidance literature:

upstream raw materials:

4-chloro-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine

(R)-1-phenyl-ethyl-amine

Downstream raw materials:

(R)-2-(4-(4-(1-phenylethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenoxy)acetonitrile

Refernces

• 1、 Kaspersen, Svein Jacob,Hoff, Bard Helge,Sundby, Eirik,Charnock, Colin. "Activity of 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines to Tetrahymena". . p. 35 - 41,7. Retrieved 2020/07/30.
• 2、 -. "MULTI-FUNCTIONAL SMALL MOLECULES AS ANTI-PROLIFERATIVE AGENTS". Page/Page column 251. . Retrieved 2008/06/13.