N₄-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-6-methylpyrimidine-2,4-diamine

Base Information

• Chemical Name: N₄-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-6-methylpyrimidine-2,4-diamine
• CAS No.: 1376514-48-5
• Molecular Formula: C₃₁H₄₅N₅O₃
• Molecular Weight: 535.73

Synonyms:N₄-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-6-methylpyrimidine-2,4-diamine

Chemical Property of N₄-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-6-methylpyrimidine-2,4-diamine

Chemical Property:

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Technology Process of N₄-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-6-methylpyrimidine-2,4-diamine

There total 13 articles about N₄-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-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: 94.0%

3-{4-[(2-amino-4-{[(3S)-1-(benzyloxy)hexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]-3-methoxyphenoxy}propyl methanesulfonate (1376514-47-4) + dimethyl amine (124-40-3) → N4-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-6-methylpyrimidine-2,4-diamine (1376514-48-5)

Guidance literature:

3-{4-[(2-amino-4-{[(3S)-1-(benzyloxy)hexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]-3-methoxyphenoxy}propyl methanesulfonate; dimethyl amine; In water; acetonitrile; at 80 ℃; for 1.5h;

With potassium carbonate; In water; acetonitrile;

Reference yield:

{4-[3-(tert-butyldimethylsilyloxy)propoxy]-2-methoxyphenyl}methanol (1256497-66-1) → N4-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-6-methylpyrimidine-2,4-diamine (1376514-48-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride; lithium chloride / tetrahydrofuran / 0.67 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

2.2: 6 h / 80 °C

3.1: methanol / 8 h / 75 °C

4.1: N,N,N'N'-tetramethyl-1,3-propanediamine / tetrahydrofuran / 3 h / 20 °C

5.1: trifluoroacetic acid / 15 h / 120 °C

6.1: hydrogenchloride / water; methanol / 1 h / 20 °C

7.1: triethylamine / tetrahydrofuran / 0 °C

8.1: acetonitrile; water / 1.5 h / 80 °C

With hydrogenchloride; N,N,N'N'-tetramethyl-1,3-propanediamine; sodium hydride; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

Reference yield:

(S)-(+)-3-amino-1-hexanol (64197-80-4) → N4-[(3S)-1-(benzyloxy)hexan-3-yl]-5-{4-[3-(dimethylamino)propoxy]-2-methoxybenzyl}-6-methylpyrimidine-2,4-diamine (1376514-48-5)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C

3: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C

4: trifluoroacetic acid / 15 h / 120 °C

5: hydrogenchloride / water; methanol / 1 h / 20 °C

6: triethylamine / tetrahydrofuran / 0 °C

7: acetonitrile; water / 1.5 h / 80 °C

With hydrogenchloride; sodium hydride; triethylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

upstream raw materials:

3-{4-[(2-amino-4-{[(3S)-1-(benzyloxy)hexan-3-yl]amino}-6-methylpyrimidin-5-yl)methyl]-3-methoxyphenoxy}propyl methanesulfonate

dimethyl amine

4-hydroxy-2-methoxybenzaldehyde

(S)-(+)-3-amino-1-hexanol

Downstream raw materials:

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

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

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