Tetrahydrofuran → HCID 86661850, compound

HRID 928354Notes

Reaction equation

HRID 928354 reaction equation
[C:1]([C:3]1[C:4]([CH3:18])=[CH:5][C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])(C)C)=[N:7][C:8]=1[CH3:9])#[N:2].[CH2:19]1COC[CH2:20]1>CO.[Ni]>[NH2:2][CH2:1][C:3]1[C:4]([CH3:18])=[CH:5][C:6]([NH:10][C:11](=[O:17])[O:12][CH2:13][CH2:16][CH2:19][CH3:20])=[N:7][C:8]=1[CH3:9]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 58081198HCID 58081198, compound

Product 1

HCID 86661850HCID 86661850, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl 5-cyano-4,6-dimethylpyridin-2-ylcarbamate (10.8 g, 43.7 mmol) in THF (100 ml) were added about 15 cm3 of a Raney-Ni suspension in MeOH under Ar. The flask was sealed, and the suspension was vigorously stirred at it for 6 d under an atmosphere of hydrogen. The reaction mixture was filtered over a plug of cellite and eluted with DCM (200 ml), DCM-MeOH (9:1, 200 ml) and NH3 in MeOH (7N, 100 ml). Removal of all volatiles in vacuo afforded the crude product which was recrystallized from MeOH-DCM to afford the title compound. LCMS RtM=1.13 min, [M+H]+=252.2.

Workup

  1. customThe flask was sealed
  2. filtrationThe reaction mixture was filtered over a plug of cellite
  3. washeluted with DCM (200 ml), DCM-MeOH (9:1, 200 ml) and NH3 in MeOH (7N, 100 ml)
  4. customRemoval of all volatiles in vacuo
  5. customafforded the crude product which
  6. customwas recrystallized from MeOH-DCM

Sources & evidence

ORD record
ord-13f93e086b254b80b5f5e4c0448aa482
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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