Hydrazine → HCID 58268931, compound

HRID 1428184Notes

Reaction equation

HRID 1428184 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([CH:10]([C:13]#[N:14])[C:11]#[N:12])[CH:3]=1.[NH2:15][NH2:16]>COCCOCCOC>[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([C:10]2[C:11]([NH2:12])=[N:15][NH:16][C:13]=2[NH2:14])[CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86653539HCID 86653539, compound

Product 1

HCID 58268931HCID 58268931, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
150 °C

Procedure

2-(6-Chloro-2-(methylthio)pyrimidin-4-yl)malononitrile (2b) (500 mg, 2.23 mmoles) was dissolved in 15 mL of diethylene glycol dimethyl ether along with of hydrazine [68.4 μL, 69.8 mg; 2.18 mmoles) and the reaction mixture sealed in a microwave vessel. The reaction was heated at 150° C. for 10 minutes (300 Watt) and then allowed to cool down. The solvent was removed under reduced pressure and the crude suspended in acetone, warmed to almost reflux and stirred. Then continued stirring while allowing to cool down to rt. The precipitate was isolated via suction filtration and washed with more acetone and air-dried. The product (3b) was obtained as a mustard colored powder (240 mg, 42% yield) and was used in the next step without further purification. LC/MS (M+1) 257, 259.

Workup

  1. custom2.18 mmoles) and the reaction mixture sealed in a microwave vessel
  2. temperatureto cool down
  3. customThe solvent was removed under reduced pressure
  4. temperaturewarmed
  5. temperatureto almost reflux
  6. stirringThen continued stirring
  7. temperatureto cool down to rt
  8. customThe precipitate was isolated via suction filtration
  9. washwashed with more acetone
  10. customair-dried

Sources & evidence

ORD record
ord-d1bac952b7fe405dadf6b7687df8002b
Source dataset
uspto-grants-2015_01
Patent number
US08937064B2

Reaction notes

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