Hydrazine hydrate (1:1) → HCID 178490034, compound

HRID 2390768Notes

Reaction equation

HRID 2390768 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([O:18][CH3:19])[CH:12]=2)=O)[CH:5]=[C:4]([NH:20][CH2:21][C@@H:22]([OH:24])[CH3:23])[N:3]=1.COC(OC)[N:28]([CH3:30])C.O.[NH2:34]N>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([O:18][CH3:19])[CH:12]=3)=[N:34][NH:28][CH:30]=2)[CH:5]=[C:4]([NH:20][CH2:21][C@@H:22]([OH:24])[CH3:23])[N:3]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 50898840HCID 50898840, compound

Product 1

HCID 178490034HCID 178490034, compoundYield 44%

Procedure

2-[2-chloro-6-(2(S)-hydroxypropylamino)pyrimidin-4-yl]-1-(3-methoxy-5-methylphenyl)ethanone (2.16 g, 6.17 mmol) was heated at 90° C. for 20 hours together with N,N-dimethylformamide dimethylacetal (8.23 mL, 61.7 mmol). Excess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation, and the reaction mixture was dissolved in anhydrous ethanol (50 mL). To this solution was dropwise added hydrazine hydrate (617 μL, 12.35 mmol), and stirred at room temperature for 12 hours. After completion of the cyclization, the solvent was removed by vacuum distillation. The concentrate was treated in water and ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under vacuum. Recrystallization in dichloromethane gave the title compound (1.01 g, 44%).

Workup

  1. customExcess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation
  2. dissolutionthe reaction mixture was dissolved in anhydrous ethanol (50 mL)
  3. customAfter completion of the cyclization, the solvent was removed by vacuum distillation
  4. additionThe concentrate was treated in water
  5. dry with materialethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationdistilled under vacuum
  8. customRecrystallization in dichloromethane

Sources & evidence

ORD record
ord-580a2492735b474ab4ceaf9c6f999cf3
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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