HCID 68569120, compound → HCID 10322398, compound

HRID 639417Notes

Reaction equation

HRID 639417 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5]1.Cl[C:20]1[N:25]=[C:24]([C:26]2[C:27]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)=[N:28][N:29]([CH3:31])[CH:30]=2)[CH:23]=[CH:22][N:21]=1>C(O)CCC.O1CCOCC1>[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([NH:18][C:20]3[N:25]=[C:24]([C:26]4[C:27]([C:32]5[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=5)=[N:28][N:29]([CH3:31])[CH:30]=4)[CH:23]=[CH:22][N:21]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 68569120HCID 68569120, compoundHCID 713791882-Chloro-4-[1-methyl-3-(4-methylphenyl)-1H-pyrazol-4-yl]pyrimidine

Product 1

HCID 10322398HCID 10322398, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3-(1-Methyl-piperidin-4-ylmethoxy)-phenylamine dihydrochloride (206 mg, 0.7 mmol) is suspended in 1.5 mL n-butanol and 1.5 mL dioxane. 2-Chloro-4-(1-methyl-3-p-tolyl-1H-pyrazol-4-yl)-pyrimidine (100 mg, 0.35 mmol) is added and the mixture heated under reflux for 15 h. The yellow suspension is evaporated to dryness and the residue portioned between 8 mL 20% potassium carbonate solution and 10 mL dichloromethane. The organic phase is dried with sodium sulfate and evaporated. The crude product is purified by flash-chromatography on Silica Gel using dichloromethane/methanol 100:1.25→100:5 and then dichloromethane/methanol/conc. ammonia 100:5:0.25→100:10:0.25. The title compound is obtained as a foam.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 15 h
  3. customThe yellow suspension is evaporated to dryness
  4. dry with materialThe organic phase is dried with sodium sulfate
  5. customevaporated
  6. customThe crude product is purified by flash-chromatography on Silica Gel

Sources & evidence

ORD record
ord-59138146c69e4073ad4cbd505887b35a
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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