Sodium hydride → HCID 66751382, compound

HRID 525278Notes

Reaction equation

HRID 525278 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1>CN(C=O)C.CCOC(C)=O>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol2×

Product 1

HCID 66751382HCID 66751382, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

As shown in step 7-i of Scheme 7, to a solution of 1,4-dioxaspiro[4.5]decan-8-ol (compound 1021, 1.0 g, 6.32 mmol) in DMF (10 mL) was added NaH (370 mg, 9.25 mmol). The reaction mixture was stirred for 20 minutes before the addition of 2-chloropyrimidine (869 mg, 7.59 mmol). The mixture was stirred for 30 minute at RT and then heated to 100° C. for 9 hours. After cooling, the mixture was diluted with EtOAc, washed with H2O, dried over Na2SO4, concentrated under reduced pressure, and purified by medium pressure silica gel chromatography (0-40% EtOAc/hexanes) to produce 2-(1,4-dioxaspiro[4.5]decan-8-yloxy)pyrimidine (compound 1022) as a colorless oil: 1H NMR (300 MHz, Chloroform-d) δ 8.52 (d, J=4.8 Hz, 2H), 6.92 (t, J=4.8 Hz, 1H), 5.15 (ddd, J=10.7, 6.5, 4.2 Hz, 1H), 4.05-3.87 (m, 4H), 2.14-1.85 (m, 6H), 1.79-1.65 (m, 2H); ESMS (M+H+)=237.12.

Workup

  1. temperatureheated to 100° C. for 9 hours
  2. temperatureAfter cooling
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by medium pressure silica gel chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7e02265c81a748258f6267987fc747ff
Source dataset
uspto-grants-2016_05
Patent number
US09340557B2

Reaction notes

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