{1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile

Base Information

• Chemical Name: {1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile
• CAS No.: 1422456-99-2
• Molecular Formula: C₃₄H₄₄F₃N₉O₃Si
• Molecular Weight: 711.863

Synonyms:{1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile

Chemical Property of {1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile

Chemical Property:

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Technology Process of {1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile

There total 9 articles about {1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile 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:

{3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride + 4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexanone (1422456-95-8) → {1-(cis-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (1422456-97-0) + {1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (1422456-99-2)

Guidance literature:

{3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride; 4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexanone; With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 25 ℃; for 16h;

With water; sodium hydrogencarbonate; In 1,2-dichloro-ethane;

Reference yield:

6-(1,4-dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidine-4-carbaldehyde (1422455-58-0) → {1-(cis-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (1422456-97-0) + {1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (1422456-99-2)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran; diethyl ether / 1 h / -78 °C

2: Dess-Martin periodane / dichloromethane / 2 h / 0 °C

3: tetrahydrofuran; diethyl ether / 1 h / -78 °C

4: hydrogenchloride; water / acetone / 5 h

5: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 25 °C

With hydrogenchloride; water; sodium tris(acetoxy)borohydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; acetone;

Reference yield:

4,4-ethylenedioxycyclohexan-1-ol (22428-87-1) → {1-(cis-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (1422456-97-0) + {1-(trans-4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (1422456-99-2)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydride / tetrahydrofuran; mineral oil / 60 h / 0 - 25 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 48 h / 110 °C

3: sodium periodate; osmium(VIII) oxide / water; 1,4-dioxane / 48 h / 25 °C

4: tetrahydrofuran; diethyl ether / 1 h / -78 °C

5: Dess-Martin periodane / dichloromethane / 2 h / 0 °C

6: tetrahydrofuran; diethyl ether / 1 h / -78 °C

7: hydrogenchloride; water / acetone / 5 h

8: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 25 °C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; sodium tris(acetoxy)borohydride; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetone; toluene; mineral oil;

upstream raw materials:

6-(1,4-dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidine-4-carbaldehyde

4-{[6-(1-hydroxy-1-methylethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexanone

4,4-ethylenedioxycyclohexan-1-ol

4,6-dichloro-2-(trifluoromethyl)pyrimidine

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