Water → HCID 59556106, compound

HRID 1173263Notes

Reaction equation

HRID 1173263 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1.[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14]1.O>C1COCC1>[N:9]1[CH:8]=[C:7]([C:19]2([OH:22])[CH2:20][CH2:21][C:16]3([O:23][CH2:13][CH2:14][O:15]3)[CH2:17][CH2:18]2)[CH:12]=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 783445-BromopyrimidineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 59556106HCID 59556106, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-butyllithium (4.32 mL of 1.6 M solution in hexane, 6.92 mmol) was added to 5-bromopyrimidine (1.0 g, 6.29 mmol) in THF (10 mL) at −78° C. with stirring under N2. After being stirred at −78° C. for 1 h, a solution of 1,4-cyclohexanedione mono-ethylene ketal (0.982 g, 6.29 mmol) in THF (10 mL) was added to the lithiated compound solution via syringe and stirred for 4 h at −78° C. Water (5 mL) was added, and the reaction mixture was warmed to room temperature and extracted using EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo and chromatographed to yield 0.18 g of 8-pyrimidin-5-yl-1,4 dioxaspiro[4,5]decan-8-ol in 12% yield. MS (E) calcd: (M+H)+=237.1; found: 237.2.

Workup

  1. stirringAfter being stirred at −78° C. for 1 h
  2. stirringstirred for 4 h at −78° C
  3. extractionextracted
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed

Sources & evidence

ORD record
ord-8890f559cfd94c9f9f5fb5bf5716a3b3
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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