6-(2,6-Dichlorophenyl)-2-[4-[2-(diethylamino)ethoxy]anilino]-8-methylpyrido[2,3-d]pyrimidin-7-one

Base Information

• Chemical Name: 6-(2,6-Dichlorophenyl)-2-[4-[2-(diethylamino)ethoxy]anilino]-8-methylpyrido[2,3-d]pyrimidin-7-one
• CAS No.: 185039-89-8
• Molecular Formula: C26H27Cl2N5O2
• Molecular Weight: 512.439
• DSSTox Substance ID: DTXSID501019043
• Nikkaji Number: J915.276H
• Wikidata: Q27088273
• Pharos Ligand ID: U4U9R4GWC9LR
• ChEMBL ID: CHEMBL49120
• Mol file: 185039-89-8.mol

Synonyms:PD 0166285;PD0166285

Chemical Property of 6-(2,6-Dichlorophenyl)-2-[4-[2-(diethylamino)ethoxy]anilino]-8-methylpyrido[2,3-d]pyrimidin-7-one

Chemical Property:

• Melting Point: 141 - 143 °C
• Boiling Point: 665.3±65.0 °C(Predicted)
• PKA: 9.65±0.25(Predicted)
• PSA: 72.28000
• Density: 1.315±0.06 g/cm3(Predicted)
• LogP: 5.83950
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 511.1541805
• Heavy Atom Count: 35
• Complexity: 719

Purity/Quality:

97% ^*data from raw suppliers

PD 0166285 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCN(CC)CCOC1=CC=C(C=C1)NC2=NC=C3C=C(C(=O)N(C3=N2)C)C4=C(C=CC=C4Cl)Cl
• Uses: PD 0166285 is a pyridopyrimidine compound that inhibits Wee1, which is a Ser/Thr kinase that regulates the cell cycle (1,2).

Technology Process of 6-(2,6-Dichlorophenyl)-2-[4-[2-(diethylamino)ethoxy]anilino]-8-methylpyrido[2,3-d]pyrimidin-7-one

There total 9 articles about 6-(2,6-Dichlorophenyl)-2-[4-[2-(diethylamino)ethoxy]anilino]-8-methylpyrido[2,3-d]pyrimidin-7-one 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:

(4-methylamino-2-methylsulfanyl-pyrimidin-5-yl)-methanol (17759-30-7) → PD-166285 (185039-89-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / MnO₂ / CHCl₃ / 6 h / Ambient temperature

2: 46 percent / K₂CO₃ / dimethylformamide / 18 h / 100 - 105 °C

3: 88 percent / 0.08 h / Heating

4: 96 percent / 6N aq. HCl / Heating

5: 92 percent / m-CPBA / CHCl₃ / 25 °C

6: glacial AcOH / 0.25 h / Heating

With hydrogenchloride; manganese(IV) oxide; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; In chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm9802259

Reference yield:

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0) → PD-166285 (185039-89-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 81 percent / Et₃N / tetrahydrofuran; H₂O / 0.5 h / 25 °C

2: 84 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / Ambient temperature

3: 93 percent / MnO₂ / CHCl₃ / 6 h / Ambient temperature

4: 46 percent / K₂CO₃ / dimethylformamide / 18 h / 100 - 105 °C

5: 88 percent / 0.08 h / Heating

6: 96 percent / 6N aq. HCl / Heating

7: 92 percent / m-CPBA / CHCl₃ / 25 °C

8: glacial AcOH / 0.25 h / Heating

With hydrogenchloride; manganese(IV) oxide; lithium aluminium tetrahydride; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/jm9802259

Reference yield:

4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (76360-82-2) → PD-166285 (185039-89-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / Ambient temperature

2: 93 percent / MnO₂ / CHCl₃ / 6 h / Ambient temperature

3: 46 percent / K₂CO₃ / dimethylformamide / 18 h / 100 - 105 °C

4: 88 percent / 0.08 h / Heating

5: 96 percent / 6N aq. HCl / Heating

6: 92 percent / m-CPBA / CHCl₃ / 25 °C

7: glacial AcOH / 0.25 h / Heating

With hydrogenchloride; manganese(IV) oxide; lithium aluminium tetrahydride; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm9802259

upstream raw materials:

4-[2-(diethylamino)ethoxy]aniline

6-(2,6-dichlorophenyl)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one

(4-methylamino-2-methylsulfanyl-pyrimidin-5-yl)-methanol

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

Downstream raw materials:

2-(4-{[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}phenoxy)-N,N-diethyl-N-[(1-methyl-4-nitro-1H-imidazol-5-yl)methyl]ethanammonium bromide