Water → 2-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

HRID 645512Notes

Reaction equation

HRID 645512 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:8]([O:14][CH2:15][CH:16]2[CH2:23][CH2:22][C:19]3([CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:9][C:10](Cl)=[N:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3].[C-]#N.[K+].C1N2CC[N:29](CC2)[CH2:28]1.O>CS(C)=O>[CH2:1]([O:4][C:5]([C:7]1[C:8]([O:14][CH2:15][CH:16]2[CH2:23][CH2:22][C:19]3([CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:9][C:10]([C:28]#[N:29])=[N:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 9237DabcoHCID 866277972-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

Product 1

HCID 687066042-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the 2-chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester (0.62 mmol) in DMSO (1.0 mL) are added KCN (0.94 mmol), DABCO (0.19 mmol), and H2O (0.10 mL) at room temperature. The reaction mixture is stirred at room temperature for 0.5 h and the reaction is quenched by the addition of water. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue is purified by silica gel column chromatography to give the titled compound; 1H NMR (CDCl3) δ 0.19-0.20 (m, 2H), 0.21-0.33 (m, 2H), 0.91-0.96 (m, 2H), 1.23-1.33 (m, 3H), 1.72-1.85 (m, 4H), 4.38 (d, 2H), 4.84 (d, 2H), 5.31-5.45 (m, 1H), 9.01 (s, 1H).

Workup

  1. customthe reaction is quenched by the addition of water
  2. extractionThe mixture is extracted with AcOEt
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-73f78fb6c2eb48488661676f59f103ca
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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