tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate

Base Information

• Chemical Name: tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate
• CAS No.: 1363161-15-2
• Molecular Formula: C₁₇H₂₂N₄O₃S
• Molecular Weight: 362.453

Synonyms:tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate

Chemical Property of tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate

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Technology Process of tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate

There total 4 articles about tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate 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: 65.0%

ethyl 4-((3-((tert-butoxycarbonyl)amino)phenyl)amino)-2-(methylthio)pyrimidine-5-carboxylate (1363161-14-1) → tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate (1363161-15-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - -20 ℃; for 4h;

Reference yield: 57.0%

ethyl 4-((3-((tert-butoxycarbonyl)amino)phenyl)amino)-2-(methylthio)pyrimidine-5-carboxylate (1363161-14-1) + tetrahydro lithium aluminum → tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate (1363161-15-2)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; methanol;

Reference yield:

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0) → tert-butyl 3-(5-(hydroxymethyl)-2-(methylmercapto)pyrimidine-4-ylamino)phenylcarbamate (1363161-15-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 80 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / -40 - 20 °C

With lithium aluminium tetrahydride; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm201591k

upstream raw materials:

ethyl 4-((3-((tert-butoxycarbonyl)amino)phenyl)amino)-2-(methylthio)pyrimidine-5-carboxylate

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

(3-aminophenyl)carbamic acid tert-butyl ester

Downstream raw materials:

N-(3-(7-(2-methoxy-4-(4-methylpiperazin-1-yl)phenylamino)-3-methyl-2-oxo-3,4-dihydropyrimido[4,5-d]pyrimidin-1(2H)-yl)phenyl)acrylamide

N-(3-(7-(4-(dimethylamino)-2-methoxyphenylamino)-3-methyl-2-oxo-3,4-dihydropyrimido[4,5-d]pyrimidin-1(2H)-yl)phenyl)acrylamide

tert-butyl 3-(3-methyl-7-(methylthio)-2-oxo-3,4-dihydropyrimido[4,5-d] pyrimidin-1(2H)-yl) phenylcarbamate

1-(3-aminophenyl)-7-(2-methoxy-4-(4-methylpiperazin-1-yl)phenylamino)-3-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

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