Hydrazine → HCID 66936083, compound

HRID 1366406Notes

Reaction equation

HRID 1366406 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH:10]([F:12])[F:11])[N:3]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C.ClCl.[NH2:31][NH2:32]>CS(C)=O>[F:11][CH:10]([F:12])[C:4]1[N:5]=[C:6]([NH:31][NH2:32])[C:7]([F:8])=[C:2]([N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)[N:3]=1

Participants

7

Reactant 5

HCID 9321HydrazineHCID 24526ChlorineHCID 531671-Methylpiperazine2×HCID 81531DiisopropylethylamineHCID 58000548HCID 58000548, compound

Product 1

HCID 66936083HCID 66936083, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4,6-Dichloro-2-(difluoromethyl)-5-fluoropyrimidine (200 mg, 0.92 mmol) was dissolved in DMSO (5 mL) and stirred at room temperature. N-methylpiperazine (110 μL, 0.96 mmol) was added, followed by DIPEA (500 μL, 2.9 mmol). The resulting mixture was stirred at room temperature for 1 hour, until the N-methylpiperazine displacement of one chlorine was complete as determined by LCMS. Hydrazine (1 mL, 31 mmol) was added and the reaction was stirred overnight at room temperature. The crude reaction mixture was purified by RP-HPLC to provide 2-(difluoromethyl)-5-fluoro-4-hydrazino-6-(4-methyl-1-piperazinyl)pyrimidine (142 mg, 56%). LCMS: (M+H)+: 277.0.

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. customThe crude reaction mixture
  3. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-ac23a443081e495c868f4b87c343a53d
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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