Isopropanol → 4,6-Diamino-2-isopropoxy-nicotinonitrile

HRID 1364519Notes

Reaction equation

HRID 1364519 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].[Na].Br[C:7]1[N:14]=[C:13]([NH2:15])[CH:12]=[C:11]([NH2:16])[C:8]=1[C:9]#[N:10]>O>[NH2:16][C:11]1[C:8]([C:9]#[N:10])=[C:7]([O:4][CH:2]([CH3:3])[CH3:1])[N:14]=[C:13]([NH2:15])[CH:12]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 1706684,6-Diamino-2-bromo-3-pyridinecarbonitrileHCID 5360545Sodium2×

Product 1

HCID 115501444,6-Diamino-2-isopropoxy-nicotinonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A heavy walled, sealable tube suitable for microwave heating was charged with 6 mL of 2-propanol and 150 mg (6.5 mmol) of sodium. The mixture was stirred at 95° C. until all of the sodium had reacted (15 minutes), then 650 mg (3.05 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 diluted with 30 mL of water. The precipitate was collected, washed with water until pH=7, then dried under reduced pressure at 95° C. to provide 312 mg (53%) of pale yellow crystals.

Workup

  1. temperatureA heavy walled, sealable tube suitable for microwave heating
  2. customhad reacted (15 minutes)
  3. customThe tube was sealed
  4. temperaturethen cooled
  5. customThe precipitate was collected
  6. washwashed with water until pH=7
  7. customdried under reduced pressure at 95° C.

Sources & evidence

ORD record
ord-5290af3b1fce4d54aa5d3f5df2b8bb97
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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