N₆-cyclohexyl-N₂-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine

Base Information

• Chemical Name: N₆-cyclohexyl-N₂-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine
• CAS No.: 1246531-30-5
• Molecular Formula: C₂₈H₃₅N₉O
• Molecular Weight: 513.646

Synonyms:N₆-cyclohexyl-N₂-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine

Chemical Property of N₆-cyclohexyl-N₂-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine

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Technology Process of N₆-cyclohexyl-N₂-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine

There total 6 articles about N₆-cyclohexyl-N₂-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine 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:

[4-(4-{[6-(cyclohexylamino)-9H-purin-2-yl]amino}-3-methoxyphenyl)piperazin-1-yl](pyridin-2-yl)methanone (1246531-29-2) → N6-cyclohexyl-N2-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine (1246531-30-5)

Guidance literature:

[4-(4-{[6-(cyclohexylamino)-9H-purin-2-yl]amino}-3-methoxyphenyl)piperazin-1-yl](pyridin-2-yl)methanone; With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 18h;

With methanol; In tetrahydrofuran;

Reference yield:

(2-chloro-9H-purin-6-yl)-cyclohexyl-amine (39639-45-7) → N6-cyclohexyl-N2-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine (1246531-30-5)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / tetrahydrofuran / Reflux

2: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 90 °C

3: hydrogenchloride / 1,4-dioxane; methanol

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

5: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; palladium diacetate; benzotriazol-1-ol; caesium carbonate; toluene-4-sulfonic acid; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; 2: Buchwald coupling;

DOI:10.1016/j.bmcl.2012.04.131

Reference yield:

tert-butyl 4-(3-methoxy-4-nitrophenyl)piperazine-1-carboxylate (1017782-79-4) → N6-cyclohexyl-N2-{2-methoxy-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]phenyl}-9H-purine-2,6-diamine (1246531-30-5)

Guidance literature:

Multi-step reaction with 5 steps

1: palladium 10% on activated carbon; hydrogen / methanol

2: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 90 °C

3: hydrogenchloride / 1,4-dioxane; methanol

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

5: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; palladium diacetate; benzotriazol-1-ol; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; 2: Buchwald coupling;

DOI:10.1016/j.bmcl.2012.04.131

upstream raw materials:

[4-(4-{[6-(cyclohexylamino)-9H-purin-2-yl]amino}-3-methoxyphenyl)piperazin-1-yl](pyridin-2-yl)methanone

(2-chloro-9H-purin-6-yl)-cyclohexyl-amine

tert-butyl 4-(3-methoxy-4-nitrophenyl)piperazine-1-carboxylate

N₆-cyclohexyl-N₂-(2-methoxy-4-piperazin-1-yl-phenyl)-9H-purine-2,6-diamine

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