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

HRID 68790

Reaction equation

HRID 68790 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]([Cl:18])=[CH:14][N:13]=1>CN(C)C=O.O1CCOCC1.C(N(CC)CC)C>[Cl: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

Participants

6

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 5906412,5-Dichloropyrimidine

Product 1

HCID 682901798-(5-Chloropyrimidin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

1,4-Dioxa-8-azaspiro[4.5]decane (2.39 g) is combined with 2,5-dichloropyrimidine (2.44 g) in N,N-dimethylformamide (50 mL), 1,4-dioxane (75 mL) and triethylamine (6.7 mL) in a glass pressure reaction vessel. The mixture is heated with stirring at 120° C. for 16 h. After cooling to room temperature, the solution is concentrated and partitioned between dichloromethane (100 mL) and water (100 mL). The aqueous layer is extracted with dichloromethane (100 mL). The dichloromethane layers are combined, washed with water (2×100 mL), dried over Na2SO4, filtered and concentrated to yield the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureAfter cooling to room temperature
  3. concentrationthe solution is concentrated
  4. custompartitioned between dichloromethane (100 mL) and water (100 mL)
  5. extractionThe aqueous layer is extracted with dichloromethane (100 mL)
  6. washwashed with water (2×100 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9a58d179ff614bf0bd54c20ea26b7417
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Linked notes

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