tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

Base Information

Chemical Name:tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate
CAS No.:1616100-66-3
Molecular Formula:C₂₅H₂₇F₂N₅O₃S
Molecular Weight:515.584
Hs Code.:

Synonyms:tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

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Chemical Property of tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

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Technology Process of tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

There total 13 articles about tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate 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: 60.0%

: 1616100-65-2
tert-butyl (4S,6S)-4-(5-bromo-2,4-difluorophenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-ylcarbamate

: 109299-78-7
pyrimidine 5-boronic acid

: 1616100-66-3
tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 100 ℃;
DOI:10.1021/acsmedchemlett.5b00432

Reference yield:

: 1616100-64-1
(4S,6S)-4-(5-bromo-2,4-difluorophenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-amine

: 1616100-66-3
tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / water; 1,4-dioxane / 12 h / 20 °C

2: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / 1,2-dimethoxyethane; ethanol; water / 0.08 h / 100 °C

With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; caesium carbonate; In 1,4-dioxane; 1,2-dimethoxyethane; ethanol; water;

Reference yield:

: 864773-64-8
1-(5-bromo-2,4-difluorophenyl)ethan-1-one

: 1616100-66-3
tert-butyl ((4S,6S)-4-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 48 h / 65 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 - 40 °C / Inert atmosphere

3.1: lithium tri-t-butoxyaluminum hydride / diethyl ether; toluene / 1.17 h / -78 - -20 °C / Inert atmosphere

4.1: hydrogenchloride / methanol; 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

5.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere

6.1: hydrogenchloride / 1,4-dioxane / 100 °C / Inert atmosphere

7.1: sodium hydrogencarbonate / water; 1,4-dioxane / 12 h / 20 °C

8.1: bis-triphenylphosphine-palladium(II) chloride; caesium carbonate / water; 1,2-dimethoxyethane; ethanol / 100 °C

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; titanium(IV) tetraethanolate; n-butyllithium; sodium hydrogencarbonate; caesium carbonate; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; toluene; 8.1: |Suzuki Coupling;
DOI:10.1021/acsmedchemlett.5b00432