Hydrazine hydrate (1:1) → 2-Hydrazinyl-4-methylpyrimidine

HRID 858825Notes

Reaction equation

HRID 858825 reaction equation
O.[NH2:2][NH2:3].[CH3:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7](SC)[N:6]=1>CCO>[CH3:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:2][NH2:3])[N:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 8212614-Methyl-2-(methylsulfanyl)pyrimidine

Product 1

HCID 123890672-Hydrazinyl-4-methylpyrimidineYield 21,562.199%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Based on a reported procedure (Vanderhaeghe, Claesen, Bull. Soc. Chim. Belg. 1959, 68, 30). Hydrazine monohydrate (334.7 ml, 6.90 mmol) was added in one portion to a solution of 4-Methyl-2-methylsulfanyl-pyrimidine (357.9 g, 2.55 mol) in abs. EtOH (890 ml). The resulting mixture was refluxed for 50 h, then hydrazine monohydrate (200 ml) was added and refluxing was continued for 50 h (the reaction was monitored by 1H NMR). Then it was cooled to 0° C. to crystallize and 213 g of crude product was isolated by filtration. Recrystallization from ethanol gave the title compound (184.7 g, 59%) as a white solid.

Workup

  1. temperatureThe resulting mixture was refluxed for 50 h
  2. temperaturerefluxing
  3. customto crystallize
  4. custom213 g of crude product was isolated by filtration
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-eeeb5cfafaa54d6fb6f6a0726e1b3d36
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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