7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Base Information

• Chemical Name: 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine
• CAS No.: 213743-31-8
• Molecular Formula: C23H22 N4 O
• Molecular Weight: 370.454
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90424958
• Nikkaji Number: J1.383.912C
• Wikidata: Q27079373
• Pharos Ligand ID: M8MXXGF3V453
• ChEMBL ID: CHEMBL47940
• Mol file: 213743-31-8.mol

Synonyms:213743-31-8;RK-24466;7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine;KIN001-051;7-Cyclopentyl-5-(4-phenoxy)phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine;MFCD04974490;KIN 001-51;RK 24466;CHEMBL47940;7-cyclopentyl-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-amine;7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine;7-CYCLOPENTYL-5-(4-PHENOXY)PHENYL-7H-PYR;4-Amino-5-(4-Phenoxyphenyl)-7h-Pyrrolo[2,3-D]pyrimidin-7-Yl-Cyclopentane;3gen;3vry;B43;NCGC00015280-01;Lopac-C-8863;D0OZ2S;Lopac0_000450;MLS002153184;SCHEMBL378454;GTPL6003;DTXSID90424958;CHEBI:180499;FMETVQKSDIOGPX-UHFFFAOYSA-N;HMS2232E04;HMS3229G15;HMS3261I22;HMS3371C06;HMS3749G17;Tox21_500450;BDBM50092228;4-Amino-7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine;7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3d]pyrimidin-4-ylamine;AKOS037648871;CCG-204542;CS-8050;LP00450;RK24466;SDCCGSBI-0050435.P003;Lck inhibitor;C8863;NCGC00015280-02;NCGC00015280-03;NCGC00015280-04;NCGC00015280-05;NCGC00015280-06;NCGC00015280-12;NCGC00093866-01;NCGC00093866-02;NCGC00261135-01;BS-15903;Lck Inhibitor - CAS 213743-31-8;SMR001230675;SY285017;HY-108318;KIN 001-51KIN 001-51;EU-0100450;S0020;A16923;C 8863;N16945;SR-01000075852;J-014016;SR-01000075852-1;Q27079373;4-Amino-5-(4-phenoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine;7-Cyclopentyl-5-(4-phenoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine;7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-4-ylamine;7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3d] pyrimidin-4-ylamine;7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, >=98% (HPLC)

Chemical Property of 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Chemical Property:

• Vapor Pressure: 1.37E-14mmHg at 25°C
• Refractive Index: 1.696
• Boiling Point: 605.1°C at 760 mmHg
• PKA: 5.75±0.30(Predicted)
• Flash Point: 319.7°C
• PSA: 65.96000
• Density: 1.3g/cm³
• LogP: 6.16910
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 17 mg/mL at ≤60 °C, soluble
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 370.17936134
• Heavy Atom Count: 28
• Complexity: 497

Purity/Quality:

98%,99%, ^*data from raw suppliers

Lck Inhibitor ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C1)N2C=C(C3=C(N=CN=C32)N)C4=CC=C(C=C4)OC5=CC=CC=C5
• Uses: Lck Inhibitor is a cell-permeable ATP-competitive inhibitor of Lck.

Technology Process of 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

There total 7 articles about 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine 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: 54.0%

5-bromo-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-4-amine + 4-phenoxyphenylboronic acid (51067-38-0) → Lck Inhibitor (213743-31-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; at 100 ℃; for 2h;

DOI:10.1039/c4md00090k

Reference yield: 31.0%

formamide (77287-34-4,77287-35-5,60100-09-6) + 2-amino-3-cyano-1-cyclopentyl-4-(4-phenoxyphenyl)pyrrole (213744-43-5) → Lck Inhibitor (213743-31-8)

Guidance literature:

With ammonia; at 200 ℃; for 2.5h;

DOI:10.1016/S0960-894X(00)00441-8

Reference yield:

4-phenoxyacetophenone (5031-78-7) → Lck Inhibitor (213743-31-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium perbromide; AcOH

2: 38 percent / toluene / 20 h / 15 - 20 °C

3: 53 percent / aq. KOH / methanol / 1 h / 65 °C

4: 31 percent / NH₃(g) / 2.5 h / 200 °C

With potassium hydroxide; ammonia; pyridinium hydrobromide perbromide; acetic acid; In methanol; toluene; 1: Bromination / 2: Alkylation / 3: Condensation / 4: Cyclization;

DOI:10.1016/S0960-894X(00)00441-8

upstream raw materials:

formamide

2-amino-3-cyano-1-cyclopentyl-4-(4-phenoxyphenyl)pyrrole

4-phenoxyacetophenone

4-(phenoxy)phenacyl bromide

Downstream raw materials:

4-amino-7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo-[2,3-d]pyrimidin-6-ylcarbonitrile

6-bromo-7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Refernces

• 1、 -. "4-AMINOPYRROLOPYRIMIDINES AS KINASE INHIBITORS". . . Retrieved 2008/06/13.
• 2、 Arnold, Lee D.,Calderwood, David J.,Dixon, Richard W.,Johnston, David N.,Kamens, Joanne S.,Munschauer, Rainer,Rafferty, Paul,Ratnofsky, Sheldon E.. "Pyrrolo[2,3-d]pyrimidines containing an extended 5-substituent as potent and selective inhibitors of lck I". . p. 2167 - 2170. Retrieved 2007/10/03.