Sodium hydride → HCID 86695236, compound

HRID 1504081Notes

Reaction equation

HRID 1504081 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[CH3:23][N:24]([CH3:32])[CH:25]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]1>C1COCC1>[CH3:23][N:24]([CH3:32])[CH:25]1[CH2:30][CH2:29][CH:28]([O:31][C:2]2[C:3]3[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 18702099trans-4-(Dimethylamino)cyclohexanolHCID 86695235HCID 86695235, compound

Product 1

HCID 86695236HCID 86695236, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-(2-[4-chlorothieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (100 mg, 0.32 mmol, 1.00 equiv) in freshly distilled THF (20 mL) was added sodium hydride (64 mg, 1.6 mmol, 5.0 equiv, 60% dispersion in mineral oil) at 0° C. under nitrogen. After stirring for 30 min at room temperature, a solution of 4-(dimethylamino)cyclohexan-1-ol (50 mg, 0.35 mmol, 1.06 equiv) was added and stirred overnight at room temperature. The reaction was then quenched by the addition of brine and extracted with EtOAc. The organic layers was combined and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was applied onto a silica gel column with DCM/MeOH (50:1-30:1) to provide 70 mg (52%) of tert-butyl N-[2-(4-[[4-(dimethylamino)cyclohexyl]oxy]thieno[2,3-d]pyrimidin-6-yl)ethyl]carbamate as a light yellow solid. MS (ES): m/z 421 (M+H)+.

Workup

  1. stirringstirred overnight at room temperature
  2. customThe reaction was then quenched by the addition of brine
  3. extractionextracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-c220d2064788407c8d2662360e30d36d
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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