Hydrazine hydrate (1:1) → HCID 57507178, compound

HRID 1907834Notes

Reaction equation

HRID 1907834 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:10]=2)[CH:5]=[C:4](Cl)[N:3]=1.O.[NH2:22][NH2:23]>O1CCOCC1.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:10]=2)[CH:5]=[C:4]([NH:22][NH2:23])[N:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57501605HCID 57501605, compound

Product 1

HCID 57507178HCID 57507178, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (2,6-dichloropyrimidin-4-yl)-(4-fluoro-3-trifluoromethylphenyl)amine (XXII) (2.5 g, 7.66 mmol) in dioxane (15 mL) was added hydrazine monohydrate (1 mL) and the mixture stirred at ambient temperature for 24 h. The mixture was diluted with water and the resulting slurry was stirred for 10 min then filtered under vacuum. The white precipitate was rinsed with water and dried under vacuum to give (2-chloro-6-hydrazinopyrimidin-4-yl)-(4-fluoro-3-trifluoromethylphenyl)amine (XXIV) as a white solid (2.1 g, 85% yield): m.p. 102-103° C., 1H NMR (CDCl3) δ 7.7 (m. 1H), 7.59 (m, 1H), 7.21 (m, 1H), 5.95 (s, 1H), 3.77 (s, 3H); ESI/MS 325 (M−H).

Workup

  1. stirringthe resulting slurry was stirred for 10 min
  2. filtrationthen filtered under vacuum
  3. washThe white precipitate was rinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-76c0fff8b43240a381a9b9e2a0516edd
Source dataset
uspto-grants-2013_12
Patent number
US08598182B2

Reaction notes

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