Hydrazine hydrate (1:1) → 4-(6-(methylthio)pyrimidin-4-yl)-1H-pyrazole-3,5-diamine

HRID 490115Notes

Reaction equation

HRID 490115 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH:9]([C:12]#[N:13])[C:10]#[N:11])[CH:4]=1.O.[NH2:15][NH2:16]>CCO>[CH3:1][S:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([C:9]2[C:10]([NH2:11])=[N:15][NH:16][C:12]=2[NH2:13])[CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 582690532-(6-(Methylthio)pyrimidin-4-yl)malononitrile

Product 1

HCID 576745294-(6-(methylthio)pyrimidin-4-yl)-1H-pyrazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(6-(methylthio)pyrimidin-4-yl)malononitrile (11.4 g, 0.06 mol) was suspended in 150 mL EtOH and hydrazine hydrate (3 mL, 0.06 mol) was added. The reaction mixture was heated to reflux for 3 days. The reaction mixture was concentrated to a solid which was suspended in ethyl acetate (100 mL), and filtered. This solid was dried to give the product, 10.4 g, 46.8 mmol, 78%, ca. 80% pure).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 days
  3. concentrationThe reaction mixture was concentrated to a solid which
  4. filtrationfiltered
  5. customThis solid was dried
  6. customto give the product, 10.4 g, 46.8 mmol, 78%, ca. 80% pure)

Sources & evidence

ORD record
ord-d12e98239fa84b6da3f39a7692751060
Source dataset
uspto-grants-2009_05
Patent number
US07528138B2

Reaction notes

Loading…