Water → HCID 25060062, compound

HRID 657808Notes

Reaction equation

HRID 657808 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:19][C:20]1[C:21]2[CH2:29][N:28]([C:30]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:31]=3[C:32]#[N:33])[CH2:27][CH2:26][C:22]=2[N:23]=[CH:24][N:25]=1)[C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[N:15][CH:16]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O.CCOC(C)=O>C1COCC1>[OH:8][CH2:9][C@@H:10]([NH:19][C:20]1[C:21]2[CH2:29][N:28]([C:30]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:31]=3[C:32]#[N:33])[CH2:27][CH2:26][C:22]=2[N:23]=[CH:24][N:25]=1)[C:11]1[CH:16]=[N:15][C:14]([O:17][CH3:18])=[N:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 69177701HCID 69177701, compound

Product 1

HCID 25060062HCID 25060062, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-2-(4-(2-(tert-butyldimethylsilyloxy)-1-(methoxypyrimidin5-yl)ethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (740 mg, 1.39 mmol) in THF (10 mL) was added 1M TBAF in THF (5 mL). The reaction mixture was stirred at room temperature for 10 minutes, and then treated with water and EtOAc. The organic layer was washed with aq. NaHCO3 and brine, dried (MgSO4), and concentrated. The residue was purified by semi-preparative HPLC to yield a white solid.

Workup

  1. washThe organic layer was washed with aq. NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by semi-preparative HPLC
  5. customto yield a white solid

Sources & evidence

ORD record
ord-36f6e397d01a4b77bab4726712777fc3
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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