HCID 86732450, compound → HCID 86732451, compound

HRID 1776425Notes

Reaction equation

HRID 1776425 reaction equation
[F:1][C:2]1[CH:32]=[C:31]([C:33]#[C:34][Si](C)(C)C)[CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:17]([O:27][CH3:28])=[CH:16][N:15]=2)=[N:6]1>O1CCCC1>[C:33]([C:31]1[CH:30]=[CH:29][C:3]([CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([C:14]3[N:19]=[C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[C:17]([O:27][CH3:28])=[CH:16][N:15]=3)=[N:6]2)=[C:2]([F:1])[CH:32]=1)#[CH:34]

Participants

3

Reactant 1

HCID 86732450HCID 86732450, compound

Product 1

HCID 86732451HCID 86732451, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

37.3 mg of 2-(1-{2-fluoro-4-[(trimethylsilyl)ethynyl]benzyl}-1H-indazol-3-yl)-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine (0.071 mmol, 1. eq.) were dissolved in 1.0 ml of dry tetrahydrofuran. 71 μl of a 1 M N,N,N-tributylbutan-1-ammonium fluoride in tetrahydrofuran (0.071 mmol, 1 eq.) were added under nitrogen atmosphere and stirred at room temperature for 18 hours. Then the mixture was partitioned between a aqueous half saturated sodium hydrogen carbonate solution and dichloromethane/isopropanol 4:1. The phases were separated and the aqueous layer was extracted twice with dichloromethane/isopropanol 4:1. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative TLC in ethyl acetate/methanol 7:3 to yield 23.2 mg (0.05 mmol, 68.4%) of the analytically pure target compound.

Workup

  1. customThen the mixture was partitioned between a aqueous half saturated sodium hydrogen carbonate solution and dichloromethane/isopropanol 4:1
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted twice with dichloromethane/isopropanol 4:1
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC in ethyl acetate/methanol 7:3
  7. customto yield 23.2 mg (0.05 mmol, 68.4%) of the analytically pure target compound

Sources & evidence

ORD record
ord-fc53ed767eb14bffa37adf293101cb8b
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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