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Water → HCID 53330914, compound

HRID 1260311
Notes
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Reaction equation

HRID 1260311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]2)=[CH:4][CH:3]=1.C[Al](C)C.C([O:20][C:21]([C:23]1[C:28]([NH:29][C:30]2[CH:31]=[N:32][CH:33]=[N:34][CH:35]=2)=[CH:27][CH:26]=[C:25]([CH3:36])[N:24]=1)=O)C.O>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([NH:13][C:21]([C:23]3[C:28]([NH:29][C:30]4[CH:35]=[N:34][CH:33]=[N:32][CH:31]=4)=[CH:27][CH:26]=[C:25]([CH3:36])[N:24]=3)=[O:20])=[N:9]2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 136269441-(4-fluorophenyl)-1H-pyrazol-3-amineHCID 16682925TrimethylaluminumHCID 583680536-Methyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 53330914HCID 53330914, compound

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

1-(4-Fluoro-phenyl)-1H-pyrazol-3-ylamine (55 mg, 0.31 mmol) was dissolved under inert gas atmosphere in dioxane (2 ml) and trimethylaluminium (0.154 ml, 2M toluene solution) was added. After stirring for 30 min at ambient temperature, 6-methyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester (A-1; 20 mg, 0.08 mmol) was added and the reaction mixture was heated at reflux for 18 hours. Upon cooling to room temperature water (0.5 ml) was added and intensive stirring was continued for 5 min. Sufficient sodium sulfate for water absorption and dichloromethane were added while stirring is continued. The resulting solution was then filtered through decalite and washed with dichloromethane. The solvent was evaporated and the final product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as off-white solid (5 mg, 16%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. additionwas added
  4. stirringintensive stirring
  5. waitwas continued for 5 min
  6. customSufficient sodium sulfate for water absorption and dichloromethane
  7. additionwere added
  8. stirringwhile stirring
  9. filtrationThe resulting solution was then filtered through decalite
  10. washwashed with dichloromethane
  11. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2adae1deadec4637bc1e209228e41307
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08470820B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes