Triethylamine → HCID 66936110, compound

HRID 1366466Notes

Reaction equation

HRID 1366466 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[N:3]=1.C(N(CC)CC)C.[CH3:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.O.[NH2:28][NH2:29]>CS(C)=O>[F:8][C:7]1[C:2]([N:19]([CH3:18])[CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[N:3][C:4]([CH3:10])=[N:5][C:6]=1[NH:28][NH2:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 81436N-Methylpyridine-4-methylamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidine

Product 1

HCID 66936110HCID 66936110, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

4,6-Dichloro-5-fluoro-2-methylpyrimidine (0.18 g, 0.99 mmol) was dissolved in DMSO (1 mL). To this solution was added triethylamine (0.15 mL, 1.08 mmol), followed by commercially available N-methyl-1-(4-pyridinyl)methanamine (0.122 g, 1.0 mmol). The reaction was left to stir for 3 hours. Then hydrazine monohydrate was added, and the resulting reaction mixture was stirred overnight at room temperature. The reaction mixture was heated to 60° C. for 90 minutes. After cooling, the reaction mixture was purified by RP-HPLC to provide 5-fluoro-6-hydrazino-N,2-dimethyl-N-(4-pyridinylmethyl)-4-pyrimidinamine (0.130 g, 49%). LCMS: (M+H)+=263.0.

Workup

  1. waitThe reaction was left
  2. customthe resulting reaction mixture
  3. stirringwas stirred overnight at room temperature
  4. temperatureAfter cooling
  5. customthe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-1ec747a1c87a483f9d22a2f0ddf42ce4
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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