methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate

Base Information

• Chemical Name: methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate
• CAS No.: 1596360-60-9
• Molecular Formula: C₁₉H₁₈FN₅O₃
• Molecular Weight: 383.382

Synonyms:methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate

Chemical Property of methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate

Chemical Property:

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Technology Process of methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate

There total 8 articles about methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate 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: 25.0%

methyl 6-(bromomethyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-2-carboxylate (1596360-16-5) + 1-(4-fluorophenyl)-2-oxo-tetrahydroimidazole (53159-75-4) → methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate (1596360-60-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1016/j.bmc.2014.02.002

Reference yield:

5-bromo-4-methylamino-pyrimidine-2-carbonitrile (1596360-12-1) → methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate (1596360-60-9)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogenchloride / 15 h / 20 °C

2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 4 h / 80 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2 h / 20 - 100 °C

4: hydrogenchloride; sodium hydrogencarbonate / methanol / 3 h / 20 °C

5: carbon tetrabromide; triphenylphosphine / dichloromethane / 3.5 h / 0 - 20 °C

6: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; carbon tetrabromide; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.02.002

Reference yield:

methyl 5-bromo-4-methylamino-pyrimidine-2-carboxylate (1523354-68-8) → methyl 6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate (1596360-60-9)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 4 h / 80 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2 h / 20 - 100 °C

3: hydrogenchloride; sodium hydrogencarbonate / methanol / 3 h / 20 °C

4: carbon tetrabromide; triphenylphosphine / dichloromethane / 3.5 h / 0 - 20 °C

5: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; carbon tetrabromide; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.02.002

upstream raw materials:

5-bromo-4-methylamino-pyrimidine-2-carbonitrile

methyl 5-bromo-4-methylamino-pyrimidine-2-carboxylate

1-(2-chloroethyl)-3-(4-fluorophenyl)urea

methyl 6-(bromomethyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-2-carboxylate

Downstream raw materials:

N-[(1S)-5-amino-1-cyano-pentyl]-6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxamide

9H-fluoren-9-ylmethyl N-[(5S)-5-cyano-5-[[6-[[3-(4-fluorophenyl)-2-oxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]pentyl]carbamate

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