N₂-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N₄-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine

Base Information

• Chemical Name: N₂-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N₄-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine
• CAS No.: 1365838-74-9
• Molecular Formula: C₂₁H₂₈N₈OS
• Molecular Weight: 440.572

Synonyms:N₂-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N₄-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine

Chemical Property of N₂-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N₄-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine

Chemical Property:

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Technology Process of N₂-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N₄-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine

There total 6 articles about N₂-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N₄-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine 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: 23.0%

N-[2-chloro-6-(4-morpholinylmethyl)-4-pyrimidinyl][1,3]thiazolo[5,4-b]pyridin-2-amine (1365838-68-1) + trans-1,4-cyclohexyldiamine (2615-25-0) → N2-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N4-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine (1365838-74-9)

Guidance literature:

In isopropyl alcohol; at 170 ℃; for 1h; Microwave irradiation;

Reference yield:

2,6-dichloropyrimidine-4-carboxylic acid methyl ester (6299-85-0) → N2-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N4-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine (1365838-74-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 96 h / 20 °C

2.1: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / tetrahydrofuran / 3 h / 20 °C

3.1: borane-THF / tetrahydrofuran / 0 - 50 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

3.3: pH 14

4.1: trifluoroacetic acid / dichloromethane / 20 - 40 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2.08 h / 20 °C / Cooling

6.1: isopropyl alcohol / 1 h / 170 °C / Microwave irradiation

With borane-THF; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; sodium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; mineral oil;

Reference yield:

2-chloro-6-(4-morpholinylcarbonyl)-N-(1,1,3,3-tetramethylbutyl)-4-pyrimidinamine (1365838-65-8) → N2-(trans-4-aminocyclohexyl)-6-(4-morpholinylmethyl)-N4-[1,3]thiazolo[5,4-b]pyridin-2-yl-2,4-pyrimidinediamine (1365838-74-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: borane-THF / tetrahydrofuran / 0 - 50 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

1.3: pH 14

2.1: trifluoroacetic acid / dichloromethane / 20 - 40 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2.08 h / 20 °C / Cooling

4.1: isopropyl alcohol / 1 h / 170 °C / Microwave irradiation

With borane-THF; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; mineral oil;

upstream raw materials:

N-[2-chloro-6-(4-morpholinylmethyl)-4-pyrimidinyl][1,3]thiazolo[5,4-b]pyridin-2-amine

trans-1,4-cyclohexyldiamine

2,6-dichloropyrimidine-4-carboxylic acid methyl ester

methyl 2-chloro-6-((2,4,4-trimethylpentan-2-yl)amino)pyrimidine-4-carboxylate

Downstream raw materials:

N-(trans-4-{[4-(4-morpholinylmethyl)-6-([1,3]thiazolo[5,4-b]pyridin-2-ylamino)-2-pyrimidinyl]amino}cyclohexyl)-2-propenamide

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