4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile

Base Information

• Chemical Name: 4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile
• CAS No.: 1227911-05-8
• Molecular Formula: C₁₇H₁₈FN₅O₂
• Molecular Weight: 343.361
• Mol file: 1227911-05-8.mol

Synonyms:4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile

Chemical Property of 4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile

There total 3 articles about 4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile 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:

(4-cyano-3-fluorophenyl)boronic acid (843663-18-3) + [(2S,5R)-4-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-2-morpholinyl]methanol (1227911-04-7) → 4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (1227911-05-8)

Guidance literature:

With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 100 - 120 ℃; Inert atmosphere; Sealed tube; microwave irradiation;

Reference yield:

[(2S,5R)-5-methyl-2-morpholinyl]methanol hydrochloride (1227911-03-6) → 4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (1227911-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 160 °C / Microwave irradiation

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / 1,4-dioxane; water / 100 - 120 °C / Microwave irradiation

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; acetonitrile; 2: Suzuki coupling;

DOI:10.1021/jm101527u

Reference yield:

(2S,5R)-5-methyl-4-(phenylmethyl)-2-morpholinylmethanol (1227911-02-5) → 4-{2-amino-6-[(2S,5R)-2-(hydroxymethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (1227911-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water / 4 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 160 °C / Microwave irradiation

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / 1,4-dioxane; water / 100 - 120 °C / Microwave irradiation

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; ethanol; water; acetonitrile; 3: Suzuki coupling;

DOI:10.1021/jm101527u

upstream raw materials:

(4-cyano-3-fluorophenyl)boronic acid

[(2S,5R)-4-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-2-morpholinyl]methanol

[(2S,5R)-5-methyl-2-morpholinyl]methanol hydrochloride

(2S,5R)-5-methyl-4-(phenylmethyl)-2-morpholinylmethanol

Downstream raw materials:

(2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-2-morpholinecarboxylic acid

(2S,5R)-4-[2-amino-6-(3-amino-1H-indazol-6-yl)-4-pyrimidinyl]-5-methyl-N-phenyl-2-morpholinecarboxamide

(2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-N-phenyl-2-morpholinecarboxamide