Hydrazine hydrate (1:1) → HCID 20805788, compound

HRID 631862Notes

Reaction equation

HRID 631862 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 20805788HCID 20805788, compound

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-d54cb5e4acd243dd83d68ec7933d6462
Source dataset
uspto-grants-2016_04
Patent number
US09321735B2

Reaction notes

Loading…