Potassium Carbonate → HCID 86614219, compound

HRID 2092304Notes

Reaction equation

HRID 2092304 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[C:20][Si](C)(C)C)[CH:14]=3)=[N:7][CH:6]=[CH:5][C:4]=2[C:3]=1[NH:25][C:26]1[C:31]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][N:33]=2)=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:19]([C:15]1[CH:14]=[C:13]([NH:12][C:8]2[C:9]3[CH:10]=[CH:11][C:2]([CH3:1])=[C:3]([NH:25][C:26]4[C:31]([C:32]5[CH:37]=[CH:36][N:35]=[CH:34][N:33]=5)=[CH:30][CH:29]=[CH:28][N:27]=4)[C:4]=3[CH:5]=[CH:6][N:7]=2)[CH:18]=[CH:17][CH:16]=1)#[CH:20]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67340174HCID 67340174, compound

Product 1

HCID 86614219HCID 86614219, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Suspended 6-methyl-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)-N1-(3-(2-(trimethylsilyl)ethynyl)phenyl)isoquinoline-1,5-diamine (0.110 g, 0.220 mmol) in methanol (2.5 mL) and added potassium carbonate (0.0607 g, 0.439 mmol). Heated to 70° C. in a sealed tube for 90 minutes. The crude mixture was diluted with water and extracted with two portions of EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated. The resulting yellow solid was recrystallized from MeOH/Et2O and filtered to afford N1-(3-ethynylphenyl)-6-methyl-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)isoquinoline-1,5-diamine. MS (M+H)+ 429.

Workup

  1. extractionextracted with two portions of EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting yellow solid was recrystallized from MeOH/Et2O
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b081cac315b94624b5263f9c39434b94
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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