Methyl Acrylate → HCID 68859189, compound

HRID 1619193Notes

Reaction equation

HRID 1619193 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][C:8]#[N:9].[C:10](OC)(=[O:13])[CH:11]=[CH2:12].CC([O-:20])(C)C.[K+].[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>>[C:8]([C:7]1([C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:23][CH:22]([C:26]([O:25][CH3:24])=[O:20])[C:10](=[O:13])[CH2:11][CH2:12]1)#[N:9]

Participants

5

Reactant 4

HCID 7294Methyl AcrylateHCID 8028TetrahydrofuranHCID 15264944(Pyrimidin-2-yl)acetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 68859189HCID 68859189, compound

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(pyrimidin-2-yl)acetonitrile (290 mg, 2.43 mmol) and methyl acrylate (462 μl, 5.11 mmol) in THF (10 mL) was added t-BuOK (1.0 M in THF, 2.92 ml, 2.92 mmol) at 0° C. After being stirred at 0° C. for 10 min and 25° C. for 50 min, the reaction mixture was quenched with ice-cold H2O, adjusted pH=4 with aqueous 10% citric acid (6 mL), and extracted (3×EtOAc). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to provide crude methyl 5-cyano-2-oxo-5-(pyrimidin-2-yl)cyclohexanecarboxylate as a dark brown solid.

Workup

  1. customthe reaction mixture was quenched with ice-cold H2O, adjusted pH=4 with aqueous 10% citric acid (6 mL)
  2. extractionextracted (3×EtOAc)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cb198e0e1d9407993e6a55171c001e5
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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