5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Base Information

• Chemical Name: 5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
• CAS No.: 926660-15-3
• Molecular Formula: C₃₅H₃₇FN₄OSSi
• Molecular Weight: 608.855

Synonyms:5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Chemical Property of 5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

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Technology Process of 5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

There total 6 articles about 5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-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: 66.0%

3-bromo-5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (926660-14-2) + 2-methylsulfanyl-4-trimethylstannanylpyrimidine (123061-59-6) → 5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (926660-15-3)

Guidance literature:

With copper(l) iodide; triphenylphosphine; lithium chloride; Pd₂(dibenzylideneacetone)2*CHCl₃; In 1,4-dioxane; at 170 ℃; for 12h;

DOI:10.1021/ja0676004

Reference yield:

(6S)-2-[4-(4-fluorophenyl)-imidazol-1-yl]-3-methylbut-3-en-1-ol (926660-13-1) → 5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (926660-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 176 mg / iPr₂NEt; 4-dimethylaminopyridine / CH₂Cl₂; dimethylformamide / 8 h / 20 °C

2: 61 percent / tricyclohexylphosphine; Mg₂Br / [RhCl(coe)2]2 / toluene / 40 h / 180 °C

3: 96 percent / Br₂ / CH₂Cl₂ / 0.25 h / -78 °C

4: 66 percent / triphenylphosphine; LiCl; CuI / Pd₂(dba)2*CHCl₃ / dioxane / 12 h / 170 °C

With dmap; copper(l) iodide; bromine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; magnesium bromide; tricyclohexylphosphine; Pd₂(dibenzylideneacetone)2*CHCl₃; [RhCl(coe)2]2; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0676004

Reference yield:

5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole → 5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (926660-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Br₂ / CH₂Cl₂ / 0.25 h / -78 °C

2: 66 percent / triphenylphosphine; LiCl; CuI / Pd₂(dba)2*CHCl₃ / dioxane / 12 h / 170 °C

With copper(l) iodide; bromine; triphenylphosphine; lithium chloride; Pd₂(dibenzylideneacetone)2*CHCl₃; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ja0676004

upstream raw materials:

3-bromo-5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

2-methylsulfanyl-4-trimethylstannanylpyrimidine

(6S)-2-[4-(4-fluorophenyl)-imidazol-1-yl]-3-methylbut-3-en-1-ol

(S_S,S)-2-methylpropane-2-sulfinic acid [1-(tert-butyldimethylsilanyloxymethyl)-2-methylallyl]-amide

Downstream raw materials:

5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

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