Hydrazine hydrate (1:1) → HCID 178505591, compound

HRID 861056Notes

Reaction equation

HRID 861056 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](/[C:8](=[CH:18]\[N:19](C)C)/[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=O)[CH:5]=[CH:4][N:3]=1.O.[NH2:23]N>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:23][NH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59038042(E)-2-(2-chloro-4-pyrimidinyl)-3-(dimethylamino)-1-(4-fluorophenyl)-2-propen-1-one

Product 1

HCID 178505591HCID 178505591, compoundYield 48.1%

Procedure

A solution of the compound prepared in step 3 (4.4 g) and hydrazine hydrate (0.82 g, 0.014 mol) was stirred at room temperature for 6 hours. The yellow precipitate was collected by filtration and air-dried to give 1.85 g of 2-chloro-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidine as a yellow solid, mp: 204–205° C.; Anal. Calc'd for C13H8ClFN4: C, 56.84; H, 2.94; N, 20.40; Cl, 12.91. Found: C, 56.43; H, 2.76; N, 20.02; Cl, 12.97.

Workup

  1. filtrationThe yellow precipitate was collected by filtration
  2. customair-dried

Sources & evidence

ORD record
ord-febc624daaef4308b146e9fa6cb68289
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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