Hydrazine → 4-Hydrazino-2-methyl-6-phenylpyrimidine trihydrochloride

HRID 2063600Notes

Reaction equation

HRID 2063600 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:14])[N:3]=1.[NH2:15][NH2:16].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[NH:15]([C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:14])[N:3]=1)[NH2:16]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 11430Potassium CarbonateHCID 7961284-Chloro-2-methyl-6-phenylpyrimidine

Product 1

HCID 602096944-Hydrazino-2-methyl-6-phenylpyrimidine trihydrochlorideYield 180.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-chloro-2-methyl-6-phenylpyrimidine (11 g, 0.0537 mol) in dioxane (100 ml) was added anhydrous hydrazine (2 g, 0.0625 mol) followed by potassium carbonate (11 g, 0.080 mol) and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was treated with 2M HCl in dioxane (100 ml) and the solid precipitated was filtered and washed with methanol (100 ml) and dried under suction to afford 10 g (60%) of the titled compound as a solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. additionThe residue was treated with 2M HCl in dioxane (100 ml)
  4. customthe solid precipitated
  5. filtrationwas filtered
  6. washwashed with methanol (100 ml)
  7. customdried under suction

Sources & evidence

ORD record
ord-6119c4f79dfb4fdc903199ef6e02519f
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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