Hydrazine hydrate (1:1) → HCID 178478395, compound

HRID 419729Notes

Reaction equation

HRID 419729 reaction equation
O.[NH2:2][NH2:3].[CH:4]1([C:7]([C:9]2[C:10](Cl)=[N:11][CH:12]=[N:13][C:14]=2[Cl:15])=O)[CH2:6][CH2:5]1>C1COCC1>[Cl:15][C:14]1[N:13]=[CH:12][N:11]=[C:10]2[NH:2][N:3]=[C:7]([CH:4]3[CH2:6][CH2:5]3)[C:9]=12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86053660HCID 86053660, compound

Product 1

HCID 178478395HCID 178478395, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add hydrazine hydrate (2.67 g, 53.4 mmol) slowly to cyclopropyl-(4,6-dichloro pyrimidin-5-yl)-methanone (9.66 g, 44.5 mmol) dissolved in 300 mL THF at room temperature and stir for 4 hours. Upon completion, partition the reaction mixture between water and ethyl acetate, collect the organic layer, wash with saturated aqueous sodium chloride, dry over anhydrous sodium sulfate, and concentrate under vacuum. Purify the resultant title compound by passing through a short silica gel (60-120 mesh) pad using Chloroform/methanol (97:3) as eluent.

Workup

  1. customUpon completion, partition the reaction mixture between water and ethyl acetate
  2. customcollect the organic layer
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate under vacuum
  6. customPurify the resultant title compound

Sources & evidence

ORD record
ord-db310854a03b4f6689be9f06799574ab
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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