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

HRID 1453281Notes

Reaction equation

HRID 1453281 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. 1H NMR (CDCl3, 300 MHz) δ, ppm: 2.40 (s, 3H), 4.00 (broad, 2H), 6.512 (d, 1H, 5 Hz), 7.03 (broad, 1H), 8.24 (d, 1H, 5 Hz).

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-6f1336d77b5c4c4883022dc01d352c40
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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