N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Base Information

• Chemical Name: N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide
• CAS No.: 1621585-88-3
• Molecular Formula: C₂₅H₂₀F₂N₄O₂S
• Molecular Weight: 478.522
• Mol file: 1621585-88-3.mol

Synonyms:N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Chemical Property of N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

There total 14 articles about N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide 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: 84.0%

(2-methylpyrimidin-5-yl)boronic acid (1034924-06-5) + (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate (1621585-55-4) → N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1621585-88-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In tetrahydrofuran; at 65 ℃; for 18.0833h;

Reference yield:

({[(2R)-2-(2,2-diethoxyethoxy)pent-4-en-1-yl]oxy}methyl)benzene (1220328-94-8) → N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1621585-88-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: formic acid / water / 2.5 h / 20 °C

1.2: 18 h / 20 °C

2.1: sodium hypochlorite / water; dichloromethane / 1.5 h / 0 - 15 °C

3.1: boron trifluoride diethyl etherate / toluene; di-isopropyl ether / 0.5 h / -76 °C

3.2: 1.5 h / -76 - -71 °C

4.1: zinc; acetic acid / 16 h / 20 - 40 °C

5.1: dichloromethane / 18 h / 20 °C

6.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 3 h / -60 - -5 °C

7.1: boron trichloride / dichloromethane; n-heptane / 4.25 h / 0 - 20 °C

8.1: triethylamine / dichloromethane / 0.08 h / 20 °C

8.2: 6.5 h / 20 °C

9.1: potassium carbonate / acetonitrile / 20.5 h / 20 °C / Inert atmosphere; Reflux

10.1: ruthenium trichloride; sodium periodate / water; acetonitrile; 1,2-dichloro-ethane / 21 h / 20 °C

11.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.43 h / -78 °C

12.1: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / tetrahydrofuran / 18.08 h / 65 °C

With pyridine; ruthenium trichloride; bis-triphenylphosphine-palladium(II) chloride; sodium hypochlorite; sodium periodate; formic acid; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; boron trichloride; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; acetic acid; triethylamine; zinc; In tetrahydrofuran; n-heptane; dichloromethane; di-isopropyl ether; water; 1,2-dichloro-ethane; toluene; acetonitrile;

Reference yield:

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4-a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide → N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(2-methylpyrimidin-5-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1621585-88-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 0.08 h / 20 °C

1.2: 6.5 h / 20 °C

2.1: potassium carbonate / acetonitrile / 20.5 h / 20 °C / Inert atmosphere; Reflux

3.1: ruthenium trichloride; sodium periodate / water; acetonitrile; 1,2-dichloro-ethane / 21 h / 20 °C

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.43 h / -78 °C

5.1: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / tetrahydrofuran / 18.08 h / 65 °C

With ruthenium trichloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;

upstream raw materials:

(2-methylpyrimidin-5-yl)boronic acid

(4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate

(4aR,6S,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-6-yl acetate

({[(2R)-2-(2,2-diethoxyethoxy)pent-4-en-1-yl]oxy}methyl)benzene