Hydrazine → 2-Chloro-5-fluoro-4-hydrazino-6-(4-methyl-1-piperazinyl)pyrimidine

HRID 1366393Notes

Reaction equation

HRID 1366393 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[C:4](Cl)[N:3]=1.CCN(C(C)C)C(C)C.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.[NH2:27][NH2:28]>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:27][NH2:28])[C:5]([F:9])=[C:4]([N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)[N:3]=1

Participants

6

Reactant 4

HCID 9321HydrazineHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 133889932,4,6-Trichloro-5-fluoropyrimidine

Product 1

HCID 866369192-Chloro-5-fluoro-4-hydrazino-6-(4-methyl-1-piperazinyl)pyrimidineYield 8.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,4,6-trichloro-5-fluoropyrimidine (402 mg, 2.0 mmol) in DMSO (3 mL) was added DIPEA (0.52 mL, 3.0 mmol), followed by N-methylpiperazine (0.24 mL, 2.2 mmol). The solution was stirred at room temperature. After 30 min, anhydrous hydrazine (1.29 mL, 99 mmol) was added, and the resulting mixture was heated at 80° C. for 30 min. After cooling to room temperature, the excess hydrazine was removed in vacuo, and the remaining solution was purified via RP-HPLC to provide the assumed 2-chloro-5-fluoro-4-hydrazino-6-(4-methyl-1-piperazinyl)pyrimidine (first eluent, 44 mg), as well as the assumed 6-chloro-5-fluoro-2-hydrazino-4-(4-methyl-1-piperazinyl)pyrimidine (second eluent, 30 mg). LCMS: (M+H)+: 261.1.

Workup

  1. temperaturethe resulting mixture was heated at 80° C. for 30 min
  2. temperatureAfter cooling to room temperature
  3. customthe excess hydrazine was removed in vacuo
  4. customthe remaining solution was purified via RP-HPLC

Sources & evidence

ORD record
ord-e8690924489c4818ae1a2ece93c1264d
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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