Dimethylformamide → 8-(Pyrimidin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1253321Notes

Reaction equation

HRID 1253321 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[O:8]1[C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>O.CCOCC>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[N:15]1[CH2:16][CH2:17][C:12]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 744042-Chloropyrimidine

Product 1

HCID 141563938-(Pyrimidin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g (0.0873 mol) of 2-chloropyrimidine, 38 g (0.2654 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 18 g (0.130 mol) of K2CO3, and 100 ml of dimethylformamide is stirred at 100°-110° C. for 4 days. The reaction mixture is allowed to cool to ambient temperature, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed copiously with water, then brine, dried over Na2SO4, and concentrated in vacuo to give a waxy solid. Trituration with ether furnishes 8.25 g (48%) of title compound: IR (KBr) 1670 and 1585 cm-1 ; NMR (CDCl3) δ 8.30 (t, 1H), 6.46 (d, 2H), 4.02 (s, 4H), 3.98-3.88 (m, 4H), and 1.90-1.66 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts are washed copiously with water
  3. dry with materialbrine, dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a waxy solid

Sources & evidence

ORD record
ord-a14fe46b71da46d7b4ddfca699eed077
Source dataset
uspto-grants-1988_05
Patent number
US04748246

Reaction notes

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