(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide

Base Information

• Chemical Name: (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide
• CAS No.: 1369763-71-2
• Molecular Formula: C₂₂H₂₂N₄O₂
• Molecular Weight: 374.442

Synonyms:(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide

Chemical Property of (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide

Chemical Property:

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Technology Process of (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide

There total 11 articles about (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide 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: 74.5%

4-aminopyridine (504-24-5) + (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-phenylcyclopropanecarboxylic acid (1369767-18-9) → (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide (1369763-71-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 - 60 ℃;

DOI:10.1021/acs.jmedchem.5b00217

Reference yield:

[(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-phenyl]cyclopropanecarbaldehyde → (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide (1369763-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; acetone / 2 h / 20 °C

2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 - 60 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.jmedchem.5b00217

Reference yield:

(1S,2R)-2-(tert-butyldiphenylsilyloxymethyl)-1-phenylcyclopropylmethanol → (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(pyridin-4-yl)-2-phenylcyclopropanecarboxamide (1369763-71-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.75 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

3.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C

3.2: 1 h / -78 - 20 °C

4.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; acetone / 2 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 - 60 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: |Mitsunobu Displacement / 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;

DOI:10.1021/acs.jmedchem.5b00217

upstream raw materials:

4-aminopyridine

(1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-phenylcyclopropanecarboxylic acid

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

((1R,2S)-2-(((2,4-dimethylpyrimidin-5-yl)oxy)methyl)-2-phenylcyclopropyl)methanol

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