Chloride → 4-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-6-hydrazino-2-methylpyrimidine

HRID 1366400Notes

Reaction equation

HRID 1366400 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[N:3]=1.[NH:11]1[CH2:15][CH:14]=[CH:13][CH2:12]1.CCN(C(C)C)C(C)C.[Cl-].[NH2:26][NH2:27]>CS(C)=O.CO>[N:11]1([C:2]2[C:7]([F:8])=[C:6]([NH:26][NH2:27])[N:5]=[C:4]([CH3:10])[N:3]=2)[CH2:15][CH:14]=[CH:13][CH2:12]1

Participants

8

Reactant 5

HCID 312Chloride2×HCID 9321HydrazineHCID 660593-PyrrolineHCID 81531DiisopropylethylamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidine

Product 1

HCID 669361874-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-6-hydrazino-2-methylpyrimidineYield 68%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

4,6-Dichloro-5-fluoro-2-methylpyrimidine (181 mg, 1.0 mmol) was dissolved in 4 mL of DMSO and stirred at room temperature. 3-Pyrroline (71 mg, 1.05 mmol) was added, followed by DIPEA (244 μL, 1.4 mmol). The resulting reaction mixture was stirred until displacement of the first chloride was complete, and then hydrazine (350 μL) and MeOH (˜2 mL) were added to the reaction mixture. The contents were then heated to 70° C. for 2 h, until displacement of the second chloride was complete. The reaction mixture was then cooled to room temperature and purified by RP-HPLC to provide 4-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-6-hydrazino-2-methylpyrimidine (142 mg, 68%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-cdcfdefa60e540db87cd497d522a6525
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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