Ethanol → 4,6-Diamino-2-ethoxypyridine-3-carbonitrile

HRID 1364511Notes

Reaction equation

HRID 1364511 reaction equation
[CH2:1]([OH:3])[CH3:2].[Na].Br[C:6]1[N:13]=[C:12]([NH2:14])[CH:11]=[C:10]([NH2:15])[C:7]=1[C:8]#[N:9]>O>[NH2:15][C:10]1[C:7]([C:8]#[N:9])=[C:6]([O:3][CH2:1][CH3:2])[N:13]=[C:12]([NH2:14])[CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1706684,6-Diamino-2-bromo-3-pyridinecarbonitrileHCID 5360545Sodium2×

Product 1

HCID 131498684,6-Diamino-2-ethoxypyridine-3-carbonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a 5 mL sealable heavy walled glass tube suitable for microwave heating containing 5 mL of absolute ethanol was added 150 mg (6.5 mmol) of sodium metal. The mixture was stirred until all of the sodium had reacted, then 1.00 g (4.71 mmol) of 2-bromo-4,6-diaminonicotinonitrile (E. I. du Pont de Nemours and Company U.S. Pat. No. 2,790,806, 1957) was added. The tube was sealed, and the reaction was heated with a microwave apparatus at 150° C. for 10 minutes then cooled and diluted with 15 mL of water. The orange precipitate which formed was washed with water until pH=7, then dried under reduced pressure at 105° C. to provide 0.545 g (65%) of a light orange solid. 1H NMR (300 MHz, d6-DMSO) δ 6.19 (s, 2H), 6.14 (s, 2H), 5.32 (s, 1H), 4.23 (q, 2H, J=7.1 Hz), 1.25 (t, 3H, J=7.1 Hz), MS (ES) m/e=151 (M−Et+H)+, 179 (M+H)+.

Workup

  1. temperatureTo a 5 mL sealable heavy walled glass tube suitable for microwave heating
  2. customhad reacted
  3. addition2,790,806, 1957) was added
  4. customThe tube was sealed
  5. temperaturethen cooled
  6. customThe orange precipitate which formed
  7. washwas washed with water until pH=7
  8. customdried under reduced pressure at 105° C.

Sources & evidence

ORD record
ord-682cdce2c8e94cce8714be14f214c135
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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