ChemicalBook CAS DataBase List 8-(5-(pyrimidin-2-yl)pyridin-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

8-(5-(pyrimidin-2-yl)pyridin-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol synthesis

4synthesis methods

Product Name:8-(5-(pyrimidin-2-yl)pyridin-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol
CAS Number:857651-05-9
Molecular formula:C17H19N3O3
Molecular Weight:313.35

31462-54-1 Synthesis

31462-54-1
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8-(5-(pyrimidin-2-yl)pyridin-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

857651-05-9
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Yield:-

Reaction Conditions:

Stage #1: 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]decan-8-olwith isopropyl magnesium chloride in tetrahydrofuran at 20 - 25; for 4.16667 h;
Stage #2: 2-iodopyrimidine;bis(acetylacetonate)nickel(II);1,2-bis-(diphenylphosphino)ethane in tetrahydrofuran at 20;

Steps:

38.A

A solution of 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (168.5 g, 0.5363 mol) in THF (2000 mL) was degassed with nitrogen for 30 minutes. A 2.0 M solution of isopropylmagnesium chloride in THF (563 mL) was added dropwise over 70 mins at room temperature to the above solution. The reaction mixture(light brownish color) was stirred for 180 minutes at 25° C. Into another flask was charged with THF (500 mL) that was degassed with nitrogen for 10 min. To it were added Nickel acetylacetonate (6.9 g, 0.027 mol) and 1,2-bis(diphenylphosphino)-ethane (11 g, 0.027 mol) under nitrogen flush, and 10 minutes later 2-iodopyrimidine (113 g, 0.536 mol). After being stirred for 30 minutes at 25° C., the resulting light green suspension was transfered to the above solution. The reaction mixture was stirred at room temperature overnight and the reaction was found to be complete by HPLC. LC-MS: found (M+H) 314.20 for desired product. The reaction mixture was directly used for next reaction.

References:

US2005/192302,2005,A1 Location in patent:Page/Page column 34-35

708274-37-7 Synthesis

8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

708274-37-7
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31462-54-1 Synthesis

31462-54-1
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$9.00/100mg

857651-05-9
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References

624-28-2 Synthesis

624-28-2
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857651-05-9
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References

4746-97-8 Synthesis

4746-97-8
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$5.00/1g

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References