Hydrazine hydrate (1:1) → 2-Chloro-4-hydrazinyl-6-phenylpyrimidine

HRID 1627432Notes

Reaction equation

HRID 1627432 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.O.[NH2:16][NH2:17]>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:16][NH2:17])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2415542,4-Dichloro-6-phenylpyrimidine

Product 1

HCID 208057882-Chloro-4-hydrazinyl-6-phenylpyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,4-dichloro-6-phenylpyrimidine (224 mg, 1 mmol) in 1 mL of 1,4-dioxane was added 300 uL of hydrazine hydrate. Stirring was continued at room temperature and the reaction monitored by thin layer chromatography (30% ethyl acetate/hexanes). When the starting material was consumed, 2 mL of water was added and the resultant precipitate was collected on a filter to afford 2-chloro-4-hydrazinyl-6-phenylpyrimidine as a yellow solid. The damp solid was suspended in 2 mL of ethanol, to which was added 220 mg of 4-trifluoromethoxybenzaldehyde. Within 5 minutes the solution became clear and then reprecipitated material. The product, 2-chloro-4-phenyl-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrimidine (XX), was collected by filtration and dried to afford 150 mg of a solid. ESI/MS 392.973, 395.002 (M+H).

Workup

  1. customwas continued at room temperature
  2. customWhen the starting material was consumed
  3. addition2 mL of water was added
  4. customthe resultant precipitate was collected on
  5. filtrationa filter

Sources & evidence

ORD record
ord-df4e90dded1440418aa6b37e32b6b052
Source dataset
uspto-grants-2014_07
Patent number
US08785630B2

Reaction notes

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