Dimethylformamide → HCID 10922518, compound

HRID 1490242Notes

Reaction equation

HRID 1490242 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)[CH:18]=[O:19]>O1CCCC1.CCCCCC>[C:1]([O:5][C:6]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[N:11][CH:10]=2)[CH2:15][CH:18]1[OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 11063649tert-butyl 4-methylpyridin-3-ylcarbamate

Product 1

HCID 10922518HCID 10922518, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 3-tert-butoxycarbonylamino-4-methylpyridine (step a, 1.47 g, 7.06 mmol) in tetrahydrofuran (50 ml) was cooled to -70° C. and treated with n-butyllithinum (6.2 ml, 2.5M in hexane, 15.5 mmol) at such a rate as to keep the temperature below -60° C. On complete addition the mixture was warmed to -20° C. and stirred for 30 minutes. The mixture was cooled to -30° C. and treated with dimethylformamide (0.66 ml, 8.47 mmol). The mixture was allowed to warm to 20° C., quenched with water (50 ml) and extracted with ethyl acetate (50 ml and 2×25 ml). The combined organic fractions were washed with saturated brine (50 ml), dried (Na2SO4), filtered and concentrated to residue in vacuo. The residue was purified by chromatography on silica gel (75% ethyl acetate/25% hexane) to afford the title compound as a colourless oil; yield: 1.26 g (81%) 1H NMR (CD2Cl2 /TMS): δ=1.6 (9H, s), 2.96 (1H, d, J=18 Hz), 3.35 (1H, dd, J=8 Hz & 18 Hz), 5.05 (1H, br.s), 5.98 (1H, br.s), 7.16 (1H, d, J=5 Hz), 8.15 (1H, d, J=5 Hz), 8.75 (1H, br.d).

Workup

  1. customthe temperature below -60° C
  2. additionOn complete addition the mixture
  3. temperatureThe mixture was cooled to -30° C.
  4. temperatureto warm to 20° C.
  5. customquenched with water (50 ml)
  6. extractionextracted with ethyl acetate (50 ml and 2×25 ml)
  7. washThe combined organic fractions were washed with saturated brine (50 ml)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated to residue in vacuo
  11. customThe residue was purified by chromatography on silica gel (75% ethyl acetate/25% hexane)

Sources & evidence

ORD record
ord-f88dae1ecf364537b82342b9d5f10514
Source dataset
uspto-grants-1997_10
Patent number
US05681959

Reaction notes

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