1-Butanol → HCID 66920846, compound

HRID 1364513Notes

Reaction equation

HRID 1364513 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[Na].Br[C:8]1[N:15]=[C:14]([NH2:16])[CH:13]=[C:12]([NH2:17])[C:9]=1[C:10]#[N:11]>C1(C)C=CC=CC=1>[NH2:17][C:12]1[C:9]([C:10]#[N:11])=[C:8]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:15]=[C:14]([NH2:16])[CH:13]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 1706684,6-Diamino-2-bromo-3-pyridinecarbonitrileHCID 5360545Sodium2×

Product 1

HCID 66920846HCID 66920846, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A heavy walled, sealable tube suitable for microwave heating was charged with 3 mL of n-butanol and 40 mg (1.7 mmol) of sodium. The mixture was stirred until all of the sodium had reacted, then 212 mg (1.00 mmol) of 2-bromo-4,6-diaminonicotinonitrile was added. The tube was sealed, and the mixture was heated with a microwave apparatus at 150° C. for 10 minutes then cooled and poured into 10 mL of toluene. The solvents were removed under reduced pressure, then the residue was partitioned between 2 mL of saturated NaHCO3(aq.) solution and 10 mL of toluene. This was concentrated again under reduced pressure, and the residue was taken up in 5 mL of water, then extracted with ethyl acetate (1×10 mL, then 2×5 mL). The combined ethyl acetate layers were back extracted with brine (1×5 mL), dried over MgSO4, filtered, and concentrated to a yellow solid. This was purified via silica gel chromatography, eluting with 50% ethyl acetate/hexanes to provide a white solid. 1H NMR (300 MHz, d6-DMSO) δ 6.19 (s, 2H), 6.14 (s, 2H), 5.31 (s, 1H), 4.18 (t, 2H, J=6.6 Hz), 2.50 (m, 1H), 1.62 (m, 2H), 1.38 (m, 2H), 0.92 (m, 3H, J=7.1 Hz); MS (ESI) m/e=151 (M−Bu+H)+, 207 (M+H)+, 205 (M−H)−.

Workup

  1. temperatureA heavy walled, sealable tube suitable for microwave heating
  2. customhad reacted
  3. customThe tube was sealed
  4. temperaturethen cooled
  5. customThe solvents were removed under reduced pressure
  6. customthe residue was partitioned between 2 mL of saturated NaHCO3(aq.) solution and 10 mL of toluene
  7. concentrationThis was concentrated again under reduced pressure
  8. extractionextracted with ethyl acetate (1×10 mL
  9. extractionThe combined ethyl acetate layers were back extracted with brine (1×5 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated to a yellow solid
  13. customThis was purified via silica gel chromatography
  14. washeluting with 50% ethyl acetate/hexanes
  15. customto provide a white solid

Sources & evidence

ORD record
ord-fbf4288048954342a6b047e0afa6bc66
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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