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

HRID 1484915Notes

Reaction equation

HRID 1484915 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([C:16]#[C:17][Si](C)(C)C)=[CH:14][N:13]=[C:12]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+]>CCO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([C:16]#[CH:17])=[CH:14][N:13]=[C:12]([N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66927380N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(piperidin-1-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine

Product 1

HCID 58169154N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-ethynyl-2-(piperidin-1-yl)pyrimidin-4-amineYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(piperidin-1-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine (101 mg, 0.27 mmol), K2CO3 (74.5 mg, 0.54 mmol, 2.0 eq) in EtOH (4 ml) was stirred at room temperature for 1 h. The mixture was filtered, the filtration was washed with water, extracted with EtOAc, dried (Na2SO4). EtOAc was removed by evaporation, the residue was recrystalized from ether to afford compound N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-ethynyl-2-(piperidin-1-yl)pyrimidin-4-amine (Compound 172) (68 mg, 81.9%). MS (m/z): 309.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.66-0.68 (m, 2H), 0.95 (d, J=6.8 Hz, 2H), 1.53 (d, J=3.6 Hz, 4H), 1.63-1.66 (m, 2H), 1.89-1.93 (m, 1H), 3.75 (t, J=5.4 Hz, 4H), 4.54 (s, 1H), 6.25 (bs, 1H), 7.94 (bs, 1H), 8.14 (s, 1H), 12.17 (bs, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe filtration
  3. washwas washed with water
  4. extractionextracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. customEtOAc was removed by evaporation
  7. customthe residue was recrystalized from ether

Sources & evidence

ORD record
ord-3a7d533a592945769ff8450ae3cce515
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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