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

Base Information

• Chemical Name: (2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-N-phenyl-2-morpholinecarboxamide
• CAS No.: 1227911-07-0
• Molecular Formula: C₂₃H₂₁FN₆O₂
• Molecular Weight: 432.457
• Mol file: 1227911-07-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-2-morpholinecarboxylic acid (1227911-06-9) + aniline (62-53-3) → (2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-N-phenyl-2-morpholinecarboxamide (1227911-07-0)

Guidance literature:

(2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-2-morpholinecarboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 0.166667h; Cooling with ice; Inert atmosphere;

aniline; In N,N-dimethyl-formamide; at 20 ℃; Cooling with ice; Inert atmosphere;

Reference yield:

[(2S,5R)-4-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-2-morpholinyl]methanol (1227911-04-7) → (2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-N-phenyl-2-morpholinecarboxamide (1227911-07-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2: chromium(VI) oxide; periodic acid / water; acetonitrile / 0 - 15 °C

3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C

With chromium(VI) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; benzotriazol-1-ol; periodic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile; 1: Suzuki coupling;

DOI:10.1021/jm101527u

Reference yield:

[(2S,5R)-5-methyl-2-morpholinyl]methanol hydrochloride (1227911-03-6) → (2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-N-phenyl-2-morpholinecarboxamide (1227911-07-0)

Guidance literature:

Multi-step reaction with 4 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

3: chromium(VI) oxide; periodic acid / water; acetonitrile / 0 - 15 °C

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C

With chromium(VI) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; benzotriazol-1-ol; periodic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile; 2: Suzuki coupling;

DOI:10.1021/jm101527u

upstream raw materials:

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

aniline

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

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

Downstream raw materials:

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