N⁴-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-diamine

Base Information

• Chemical Name: N⁴-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-diamine
• CAS No.: 1352624-47-5
• Molecular Formula: C₃₃H₃₇FN₆OSi
• Molecular Weight: 580.78

Synonyms:N⁴-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-diamine

Chemical Property of N⁴-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-diamine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-diamine

There total 10 articles about N⁴-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-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: 82.0%

N-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-5-nitropyrimidin-4-amine (1352624-46-4) → N4-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-diamine (1352624-47-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 6h;

DOI:10.1021/acs.jmedchem.9b00533

Reference yield: 82.0%

→ N4-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-diamine (1352624-47-5)

Guidance literature:

Reference yield:

6-fluoroimidazo[1,2-a]pyridine-3-carbonitrile (1134327-96-0) → N4-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,5-diamine (1352624-47-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium methylate / methanol / 72 h / 20 °C

1.2: 24 h / Microbiological reaction

2.1: triethylamine / ethanol / 22 h / 90 °C / Sealed tube

3.1: trichlorophosphate / 2 h / 90 °C / Sealed tube

4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

5.1: hydrogen; palladium 10% on activated carbon / ethanol / 6 h / 20 °C

With palladium 10% on activated carbon; hydrogen; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/acs.jmedchem.9b00533

upstream raw materials:

2,2,2-trifluoro-N-((1r,4r)-4-hydroxycyclohexyl)acetamide

trans-4-hydroxycyclohexylamine

N-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2,2,2-trifluoroacetamide

6-fluoroimidazo[1,2-a]pyridine-3-carbonitrile

Downstream raw materials:

9-((1r,4r)-4-(tert-butyldiphenylsilyloxy)cyclohexyl)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-7H-purin-8(9H)-one

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