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

Base Information

• Chemical Name: 2-(trans-4-(2-amino-5-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol
• CAS No.: 1552301-32-2
• Molecular Formula: C₂₁H₂₇N₅O₃
• Molecular Weight: 397.477

Synonyms:2-(trans-4-(2-amino-5-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol

Chemical Property of 2-(trans-4-(2-amino-5-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol

Chemical Property:

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Technology Process of 2-(trans-4-(2-amino-5-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol

There total 9 articles about 2-(trans-4-(2-amino-5-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol 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: 74.0%

2-(trans-4-(2-amino-5-bromo-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol + 2-methoxy-pyridine-5-boronic acid (163105-89-3,600726-67-8) → 2-(trans-4-(2-amino-5-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol (1552301-32-2)

Guidance literature:

With bis(triphenylphosphine)palladium(II) chloride; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2013.12.112

Reference yield:

2-amino-6-methyl-4-chloropyrimidine (5600-21-5) → 2-(trans-4-(2-amino-5-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol (1552301-32-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-iodo-succinimide / water / 20 °C

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

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

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

5.1: potassium tert-butylate / tert-butyl alcohol / 24 h / 90 °C / Inert atmosphere

6.1: sodium hydride / mineral oil / 2.5 h / 0 °C

6.2: 0 °C

6.3: 3 h / 40 °C

7.1: hydroxylamine hydrochloride / water; ethanol / Reflux

8.1: bromine / dichloromethane / 1 h / 20 °C

9.1: potassium carbonate; bis(triphenylphosphine)palladium(II) chloride / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; N-iodo-succinimide; copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; hydroxylamine hydrochloride; potassium tert-butylate; bromine; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2013.12.112

Reference yield:

4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (897030-99-8) → 2-(trans-4-(2-amino-5-(6-methoxypyridin-3-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexyloxy)ethanol (1552301-32-2)

Guidance literature:

Multi-step reaction with 8 steps

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

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

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

4.1: potassium tert-butylate / tert-butyl alcohol / 24 h / 90 °C / Inert atmosphere

5.1: sodium hydride / mineral oil / 2.5 h / 0 °C

5.2: 0 °C

5.3: 3 h / 40 °C

6.1: hydroxylamine hydrochloride / water; ethanol / Reflux

7.1: bromine / dichloromethane / 1 h / 20 °C

8.1: potassium carbonate; bis(triphenylphosphine)palladium(II) chloride / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; hydroxylamine hydrochloride; potassium tert-butylate; bromine; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2013.12.112

upstream raw materials:

2-methoxy-pyridine-5-boronic acid

2-amino-6-methyl-4-chloropyrimidine

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

4-chloro-2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-iodo-6-methylpyrimidine

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