trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol

Base Information

• Chemical Name: trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol
• CAS No.: 1552301-38-8
• Molecular Formula: C₂₅H₂₉N₅O₂
• Molecular Weight: 431.538

Synonyms:trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol

Chemical Property of trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol

There total 6 articles about trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol 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: 46.0%

2-methoxy-5-bromopyridine (13472-85-0,1199266-76-6) + trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-ethynyl-6-methylpyrimidin-4-ylamino)cyclohexanol (1552301-36-6) → trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol (1552301-38-8)

Guidance literature:

With copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 75 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2013.12.112

Reference yield:

2-amino-6-methyl-4-chloropyrimidine (5600-21-5) → trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol (1552301-38-8)

Guidance literature:

Multi-step reaction with 6 steps

1: N-iodo-succinimide / water / 20 °C

2: toluene-4-sulfonic acid / toluene / 6 h / Dean-Stark; Reflux

3: N-ethyl-N,N-diisopropylamine; 1-methyl-pyrrolidin-2-one / 24 h / 160 °C / Sealed tube

4: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 70 °C / Inert atmosphere

5: potassium carbonate / methanol / 0.75 h / 20 °C

6: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 75 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; N-iodo-succinimide; copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; water; toluene;

DOI:10.1016/j.bmcl.2013.12.112

Reference yield:

4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (897030-99-8) → trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((6-methoxypyridin-3-yl)ethynyl)-6-methylpyrimidin-4-ylamino)cyclohexanol (1552301-38-8)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / toluene / 6 h / Dean-Stark; Reflux

2: N-ethyl-N,N-diisopropylamine; 1-methyl-pyrrolidin-2-one / 24 h / 160 °C / Sealed tube

3: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 70 °C / Inert atmosphere

4: potassium carbonate / methanol / 0.75 h / 20 °C

5: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 75 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; toluene;

DOI:10.1016/j.bmcl.2013.12.112

upstream raw materials:

2-methoxy-5-bromopyridine

trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-ethynyl-6-methylpyrimidin-4-ylamino)cyclohexanol

2-amino-6-methyl-4-chloropyrimidine

4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine

Downstream raw materials:

C₂₅H₂₉N₅O₂

2-(trans-4-(2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol

2-(trans-4-(2-amino-6-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol

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