Piperidine → N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(piperidin-1-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine

HRID 1484914Notes

Reaction equation

HRID 1484914 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([C:17]#[C:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH:4][N:3]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CC(O)C>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[C:5]([C:17]#[C:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH:4][N:3]=[C:2]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 581691392-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine

Product 1

HCID 66927380N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(piperidin-1-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amineYield 44.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl) pyrimidin-4-amine (200 mg, 0.6 mmol, 1.0 eq), piperidine (102.7 mg, 1.2 mmol, 2.0 eq) in iPrOH (4 ml) was stirred at room temperature for 2 h. Then the mixture was washed with water, extracted with EtOAc, dried (Na2SO4). EtOAc was removed by evaporation and the residue was recrystalized by PE to give compound N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(piperidin-1-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine (101 mg, 44.3%).

Workup

  1. washThen the mixture was washed with water
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. customEtOAc was removed by evaporation
  5. customthe residue was recrystalized by PE

Sources & evidence

ORD record
ord-74dc2f54e3f74123848bcc524707ed83
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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