1,4-Dioxa-8-azaspiro(4.5)decane → HCID 23447583, compound

HRID 1840581Notes

Reaction equation

HRID 1840581 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.C(N(C(C)C)CC)(C)C.[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[CH:23][N:22]=1>C(O)C>[Cl:20][C:21]1[N:22]=[CH:23][N:24]=[C:25]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[CH:26]=1

Participants

5

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 23447583HCID 23447583, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,4-dioxa-8-azaspiro[4,5]decane (9.02 g) and diisopropylethylamine (9.77 g) in ethanol (30 ml) was added 4,6-dichloropyrimidine (9.88 g), and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated, and the residue was diluted with dichloromethane (150 ml). The mixture was washed with 0.3N sodium hydroxide solution and saturated brine, dried and concentrated, and the residue was crystallized from diethylether to give colorless crystals of 8-(6-chloropyrimidine-4-yl)-1,4-dioxa-8-azaspiro[4,5]decane (15.84 g).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was diluted with dichloromethane (150 ml)
  3. washThe mixture was washed with 0.3N sodium hydroxide solution and saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was crystallized from diethylether

Sources & evidence

ORD record
ord-1e70f6056fdd41c38e0392c33300dbb6
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

Loading…