1,4-Dioxa-8-azaspiro(4.5)decane → HCID 22329430, compound

HRID 586414Notes

Reaction equation

HRID 586414 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:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[C:14]([Cl:19])[N:13]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:11][C:12]1[N:17]=[C:16]([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:15]=[C:14]([Cl:19])[N:13]=1

Participants

5

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 773782,4,6-TrichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 22329430HCID 22329430, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1,4-dioxa-8-azaspiro[4.5]decane (19.52 g, 136.3 mmol) was added to a solution of 2,4,6-trichloropyrimidine (25.0 g, 136 mmol) in CH2Cl2 (475 mL) at −78° C. with vigorous stirring. Diisopropylethylamine (26.4 g, 205 mmol) was added dropwise to the above mixture and stirred for 3 hours at −78° C. The resulting mixture was brought to 0° C. over a period of 3 hours and quenched with water (250 mL). The organic layer was separated, washed with aqueous citric acid (2×100 mL), brine (2×200 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography [eluent: EtOAc/hexanes (1:9)], giving the desired product (7.40 g, 19%).

Workup

  1. waitThe resulting mixture was brought to 0° C. over a period of 3 hours
  2. customquenched with water (250 mL)
  3. customThe organic layer was separated
  4. washwashed with aqueous citric acid (2×100 mL), brine (2×200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography [eluent: EtOAc/hexanes (1:9)]

Sources & evidence

ORD record
ord-81f3fbfdb1794a0da04a4edfc344bd7f
Source dataset
uspto-grants-2005_08
Patent number
US06936607B2

Reaction notes

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