5-[4-(benzyloxy)-2-methoxybenzyl]-N₄-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-diamine

Base Information

• Chemical Name: 5-[4-(benzyloxy)-2-methoxybenzyl]-N₄-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-diamine
• CAS No.: 1376514-61-2
• Molecular Formula: C₃₂H₄₈N₄O₃Si
• Molecular Weight: 564.844

Synonyms:5-[4-(benzyloxy)-2-methoxybenzyl]-N₄-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-diamine

Chemical Property of 5-[4-(benzyloxy)-2-methoxybenzyl]-N₄-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-diamine

Chemical Property:

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Technology Process of 5-[4-(benzyloxy)-2-methoxybenzyl]-N₄-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-diamine

There total 5 articles about 5-[4-(benzyloxy)-2-methoxybenzyl]-N₄-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-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:

(3S)-3-({2-amino-5-[4-(benzyloxy)-2-methoxybenzyl]-6-methylpyrimidin-4-yl}amino)-hexan-1-ol (1376514-59-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-[4-(benzyloxy)-2-methoxybenzyl]-N4-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-diamine (1376514-61-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 27h; Inert atmosphere;

Reference yield:

4-benzyloxy-1-bromo-2-methoxybenzene (171768-67-5) → 5-[4-(benzyloxy)-2-methoxybenzyl]-N4-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-diamine (1376514-61-2)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrabutyl-ammonium chloride; N-Methyldicyclohexylamine / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / N,N-dimethyl-formamide / 18 h / 100 °C / Inert atmosphere

2: methanol / 5 h / 60 °C

3: 1,4-diaza-bicyclo[2.2.2]octane / tetrahydrofuran / 3 h / 50 °C

4: trifluoroacetic acid / propyl cyanide / 20 h / 120 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 27 h / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; N-Methyldicyclohexylamine; tetrabutyl-ammonium chloride; trifluoroacetic acid; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In tetrahydrofuran; methanol; propyl cyanide; N,N-dimethyl-formamide; 1: Heck Reaction;

Reference yield:

2-amino-5-[4-(benzyloxy)-2-methoxybenzyl]-6-methylpyrimidin-4-ol (1376514-55-4) → 5-[4-(benzyloxy)-2-methoxybenzyl]-N4-[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]-6-methylpyrimidine-2,4-diamine (1376514-61-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,4-diaza-bicyclo[2.2.2]octane / tetrahydrofuran / 3 h / 50 °C

2: trifluoroacetic acid / propyl cyanide / 20 h / 120 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 27 h / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; trifluoroacetic acid; In tetrahydrofuran; propyl cyanide; N,N-dimethyl-formamide;

upstream raw materials:

(3S)-3-({2-amino-5-[4-(benzyloxy)-2-methoxybenzyl]-6-methylpyrimidin-4-yl}amino)-hexan-1-ol

tert-butyldimethylsilyl chloride

4-benzyloxy-1-bromo-2-methoxybenzene

methyl 2-[4-(benzyloxy)-2-methoxybenzyl]-3-oxobutanoate

Downstream raw materials:

4-[(2-amino-4-{[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]amino}-6-methyl-pyrimidin-5-yl)methyl]-3-methoxyphenol

2-[(2-amino-4-{[(3S)-1-hydroxyhexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]-5-[2-(dimethylamino)ethoxy]phenol

(3S)-3-[(2-amino-5-{4-[2-(dimethylamino)ethoxy]-2-methoxybenzyl}-6-methylpyrimidin-4-yl)amino]hexan-1-ol

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