Tetrahydrofuran → HCID 117902792, compound

HRID 923663Notes

Reaction equation

HRID 923663 reaction equation
[C:1]([O:5][C:6](=[O:43])[N:7]([CH:9]([C:11](=[O:42])[NH:12][C:13]1[CH:18]=[C:17]([C:19]2[C:20]3[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[C:21]=3[N:22]=[CH:23][N:24]=2)[CH:16]=[C:15]([C:30]#[C:31][Si](C(C)C)(C(C)C)C(C)C)[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:43])[N:7]([CH:9]([C:11](=[O:42])[NH:12][C:13]1[CH:18]=[C:17]([C:19]2[C:20]3[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[C:21]=3[N:22]=[CH:23][N:24]=2)[CH:16]=[C:15]([C:30]#[CH:31])[N:14]=1)[CH3:10])[CH3:8])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 123481016HCID 123481016, compound

Product 1

HCID 117902792HCID 117902792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-{1-[(4-{1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-{2-[tris(propan-2-yl)silyl]ethynyl}pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate D1 (0.52 g, 0.86 mmol), THF (10 ml) and tetrabutylammonium fluoride (1 mol/l solution in THF, 0.95 ml, 0.95 mmol) is stirred at RT for 1 h. The mixture is diluted with DCM and extracted with a saturated aqueous solution of sodium hydrogencarbonate and brine. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The crude product is used in the next step without further purification.

Workup

  1. extractionextracted with a saturated aqueous solution of sodium hydrogencarbonate and brine
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product is used in the next step without further purification

Sources & evidence

ORD record
ord-264496eda8fd4dc088738dd2edbb2e9a
Source dataset
uspto-grants-2016_03
Patent number
US09278978B2

Reaction notes

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