2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

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Chemical Name:2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
CAS No.:471844-88-9
Molecular Formula:C₂₆H₂₅FN₄O₂S
Molecular Weight:476.575
Hs Code.:

2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5<i>H</i>-pyrrolo[1,2-<i>a</i>]imidazole

Synonyms:2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

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Chemical Property of 2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

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Technology Process of 2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

There total 12 articles about 2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 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: 48.0%

: 471844-84-5
2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

: 1122-74-3
4-iodo-2-(methylthio)pyrimidine

: 471844-88-9
2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Guidance literature:: 2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

With tributyltin iodide;

4-iodo-2-(methylthio)pyrimidine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; for 96h;
DOI:10.1016/j.bmcl.2005.07.076

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 471844-88-9
2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Guidance literature:: Multi-step reaction with 9 steps

1.1: imidazole / dimethylformamide / 2 h / 20 °C

2.1: Lawesson's reagent / tetrahydrofuran / 2 h / 20 °C

3.1: CH₂Cl₂ / 5 h / 20 °C

4.1: NH₄Cl / methanol / 3.5 h / 50 °C

5.1: ethyl acetate / 16 h / 20 °C

6.1: HBr; AcOH / aq. ethanol / 5.5 h / Heating

7.1: TBAF / tetrahydrofuran / 1 h / 0 - 20 °C

8.1: 99 percent / aq. NaOH; n-Bu₄NHSO₄ / 12 h / 20 °C

9.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

9.2: Bu₃SnI

9.3: 48 percent / Pd(PPh₃)4 / dimethylformamide / 96 h / 80 °C

With Lawessons reagent; 1H-imidazole; sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; acetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 9.3: Stille coupling;
DOI:10.1016/j.bmcl.2005.07.076

Reference yield:

: 852674-75-0
2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methylsulfanyl-3,4-dihydro-2H-pyrrole

: 471844-88-9
2-(4-fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Guidance literature:: Multi-step reaction with 6 steps

1.1: NH₄Cl / methanol / 3.5 h / 50 °C

2.1: ethyl acetate / 16 h / 20 °C

3.1: HBr; AcOH / aq. ethanol / 5.5 h / Heating

4.1: TBAF / tetrahydrofuran / 1 h / 0 - 20 °C

5.1: 99 percent / aq. NaOH; n-Bu₄NHSO₄ / 12 h / 20 °C

6.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

6.2: Bu₃SnI

6.3: 48 percent / Pd(PPh₃)4 / dimethylformamide / 96 h / 80 °C

With sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; acetic acid; In tetrahydrofuran; methanol; ethanol; ethyl acetate; 6.3: Stille coupling;
DOI:10.1016/j.bmcl.2005.07.076