Tetrahydrofurfuryl alcohol → (Racemic) 6-amino-4-((tetrahydrofuran-2-yl)methoxy)nicotinonitrile

HRID 1777879Notes

Reaction equation

HRID 1777879 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8](Cl)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[O:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17].CC(N(C)C)=O.[H-].[Na+]>CCOC(C)=O>[NH2:1][C:2]1[CH:9]=[C:8]([O:17][CH2:16][CH:12]2[CH2:13][CH2:14][CH2:15][O:11]2)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 7360Tetrahydrofurfuryl alcoholHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 219492196-Amino-4-chloro-3-pyridinecarbonitrile2×

Product 1

HCID 118036975(Racemic) 6-amino-4-((tetrahydrofuran-2-yl)methoxy)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

6-amino-4-chloronicotinonitrile (intermediate 16, 70 mg, 0.456 mmol) and (tetrahydrofuran-2-yl)methanol (233 mg, 2.28 mmol) were charged into a vial. DMA (1 ml) was added to the mixture at room temperature followed by NaH (60% in mineral oil dispersion, 109 mg, 2.73 mmol). The mixture was then heated at 70° C. for 16 h. The reaction mixture was cooled to room temperature, diluted in EtOAc and washed with aq. pH7 buffer (2×) and brine. The organic layer was dried over

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with aq. pH7 buffer (2×) and brine
  3. customThe organic layer was dried over

Sources & evidence

ORD record
ord-6346b5d6520c4a73b8671c8db3930a11
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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