2-(4-Fluorophenyl)-5-((methoxycarbonyl)amino)pyrimidin-4-one-3-ethanoylvaline-trifluoromethylketone

Base Information

Chemical Name:2-(4-Fluorophenyl)-5-((methoxycarbonyl)amino)pyrimidin-4-one-3-ethanoylvaline-trifluoromethylketone
CAS No.:154753-62-5
Molecular Formula:C₂₀H₂₀F₄N₄O₅
Molecular Weight:472.396
Hs Code.:
DSSTox Substance ID:DTXSID00935060
Nikkaji Number:J589.888I
Pharos Ligand ID:FLJSJPNA1LAD
ChEMBL ID:CHEMBL11336
Mol file:154753-62-5.mol

Synonyms:2-(4-fluorophenyl)-5-((methoxycarbonyl)amino)pyrimidin-4-one-3-ethanoylvaline-trifluoromethylketone;3-aminopyrimidine-TFMK

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Chemical Property of 2-(4-Fluorophenyl)-5-((methoxycarbonyl)amino)pyrimidin-4-one-3-ethanoylvaline-trifluoromethylketone

Chemical Property:

PSA：126.37000
LogP:3.35380
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:8
Exact Mass:472.13698240
Heavy Atom Count:33
Complexity:848

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)C(C(=O)C(F)(F)F)NC(=O)CN1C(=NC=C(C1=O)NC(=O)OC)C2=CC=C(C=C2)F

Technology Process of 2-(4-Fluorophenyl)-5-((methoxycarbonyl)amino)pyrimidin-4-one-3-ethanoylvaline-trifluoromethylketone

There total 10 articles about 2-(4-Fluorophenyl)-5-((methoxycarbonyl)amino)pyrimidin-4-one-3-ethanoylvaline-trifluoromethylketone 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:

: 1194-02-1,143234-87-1
4-fluorobenzonitrile

: 154753-62-5
{2-(4-Fluoro-phenyl)-6-oxo-1-[(3,3,3-trifluoro-1-isopropyl-2-oxo-propylcarbamoyl)-methyl]-1,6-dihydro-pyrimidin-5-yl}-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 103.1 g / HCl / ethanol / 16 h / Ambient temperature

2: 53 percent / methanol / 72 h / 5 °C

3: 73 percent / methanol / 1.5 h / 100 °C

4: 89 percent / pyridine, lithium iodide / 2 h / Heating

5: 1.) Et₃N, diphenyl phosphorazidate / 1.) 100 deg C, 2 h, 2.) 100 deg C, 12 h

6: 1N aq. HCl / tetrahydrofuran / 8 h / Heating

7: sodium chlorite, sodium dihydrogen phosphate monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature

8: 1-hydroxybenzotriazole hydrate, Et₃N, EDC / dimethylformamide / 16 h

9: anisole, trifluoromethanesulfonic acid / CH₂Cl₂ / 0.25 h / 0 - 20 °C

10: Et₃N / CH₂Cl₂

With pyridine; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; trifluorormethanesulfonic acid; diphenyl phosphoryl azide; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; triethylamine; lithium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jm00001a015

Reference yield:

: 149742-99-4
methyl 1-(2,2-dimethoxyethyl)-2-(4-fluorophenyl)pyrimidin-6(1H)-one-5-carboxylate

: 154753-62-5
{2-(4-Fluoro-phenyl)-6-oxo-1-[(3,3,3-trifluoro-1-isopropyl-2-oxo-propylcarbamoyl)-methyl]-1,6-dihydro-pyrimidin-5-yl}-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / pyridine, lithium iodide / 2 h / Heating

2: 1.) Et₃N, diphenyl phosphorazidate / 1.) 100 deg C, 2 h, 2.) 100 deg C, 12 h

3: 1N aq. HCl / tetrahydrofuran / 8 h / Heating

4: sodium chlorite, sodium dihydrogen phosphate monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature

5: 1-hydroxybenzotriazole hydrate, Et₃N, EDC / dimethylformamide / 16 h

6: anisole, trifluoromethanesulfonic acid / CH₂Cl₂ / 0.25 h / 0 - 20 °C

7: Et₃N / CH₂Cl₂

With pyridine; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; trifluorormethanesulfonic acid; diphenyl phosphoryl azide; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; triethylamine; lithium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jm00001a015

Reference yield:

: 149742-96-1
N-(2,2-dimethoxyethyl)-4-(fluorophenyl)carboxamidine

: 154753-62-5
{2-(4-Fluoro-phenyl)-6-oxo-1-[(3,3,3-trifluoro-1-isopropyl-2-oxo-propylcarbamoyl)-methyl]-1,6-dihydro-pyrimidin-5-yl}-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 73 percent / methanol / 1.5 h / 100 °C

2: 89 percent / pyridine, lithium iodide / 2 h / Heating

3: 1.) Et₃N, diphenyl phosphorazidate / 1.) 100 deg C, 2 h, 2.) 100 deg C, 12 h

4: 1N aq. HCl / tetrahydrofuran / 8 h / Heating

5: sodium chlorite, sodium dihydrogen phosphate monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature

6: 1-hydroxybenzotriazole hydrate, Et₃N, EDC / dimethylformamide / 16 h

7: anisole, trifluoromethanesulfonic acid / CH₂Cl₂ / 0.25 h / 0 - 20 °C

8: Et₃N / CH₂Cl₂

With pyridine; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; trifluorormethanesulfonic acid; diphenyl phosphoryl azide; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; triethylamine; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jm00001a015