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Water → tert-butyl (5-(2-((4-cyanophenyl)amino)-4-(1H-pyrazol-1-yl)pyrimidin-5-yl)-4-pentyn-1-yl)carbamate

HRID 2284818
Notes
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Reaction equation

HRID 2284818 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:6][N:5]=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[N:3]=1.[NH:30]1[CH:34]=[CH:33][CH:32]=[N:31]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1CCCC1=O.C(OCC)(=O)C>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:4]2[N:3]=[C:2]([N:30]3[CH:34]=[CH:33][CH:32]=[N:31]3)[C:7]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:6][N:5]=2)=[CH:23][CH:24]=1)#[N:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 10796Cesium carbonateHCID 90052206Tert-butyl (5-(4-chloro-2-((4-cyanophenyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)carbamate

Product 1

HCID 90051821tert-butyl (5-(2-((4-cyanophenyl)amino)-4-(1H-pyrazol-1-yl)pyrimidin-5-yl)-4-pentyn-1-yl)carbamateYield 61.9%

Reagents, catalysts & solvents

2
HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (5-(4-chloro-2-((4-cyanophenyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)carbamate (T5, 30 mg) and pyrazole (7 mg) in N-methylpyrrolidone (1 mL), cesium carbonate (71 mg) was added at room temperature, and the mixture was stirred at 60° C. for 3 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 90 to 40% hexane in ethyl acetate) to obtain tert-butyl (5-(2-((4-cyanophenyl)amino)-4-(1H-pyrazol-1-yl)pyrimidin-5-yl)-4-pentyn-1-yl)carbamate (T7, 20 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 90 to 40% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-bc815e0405a2446cb9d19ca6f70fb7b9
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145415B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes