1,4-Dioxa-8-azaspiro(4.5)decane → 8-(5-Ethylpyrimidin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1409702Notes

Reaction equation

HRID 1409702 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl[C:12]1[N:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][N:13]=1.C(N(C(C)C)C(C)C)C>O1CCCC1.ClCCl>[CH2:18]([C:15]1[CH:14]=[N:13][C:12]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)=[N:17][CH:16]=1)[CH3:19]

Participants

6

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidine

Product 1

HCID 682902468-(5-Ethylpyrimidin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,4-dioxa-8-aza-spiro[4.5]decane (11.08 mL), 2-chloro-5-ethylpyrimidine (7.50 mL), and ethyldiisopropylamine (15.50 mL) in tetrahydrofuran (60 mL) is heated under reflux for 30 min. After cooling to room temperature, the reaction mixture is diluted with dichloromethane and washed with 0.1 M citric acid and brine. The aqueous phase is basified with 1 M aqueous NaOH solution and extracted with dichloromethane. The combined organic phases are dried over MgSO4 and the solvent is evaporated in vacuo to give the title compound. LC (method 11): tR=1.10 min; Mass spectrum (ESI+): m/z=250 [M+H]+.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 min
  3. washwashed with 0.1 M citric acid and brine
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-6e0fe149a6e348e19ac19741949e2208
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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