Sodium hydride → HCID 86695246, compound

HRID 1504082Notes

Reaction equation

HRID 1504082 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:17]1[C:18]2[CH:25]=[C:24]([CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[S:23][C:19]=2[N:20]=[CH:21][N:22]=1>C1COCC1>[N:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([O:13][C:17]3[C:18]4[CH:25]=[C:24]([CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[S:23][C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:11][CH2:12]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 582055574-(Morpholin-4-yl)cyclohexan-1-olHCID 86695235HCID 86695235, compound

Product 1

HCID 86695246HCID 86695246, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(morpholin-4-yl)cyclohexan-1-ol (143 mg, 0.77 mmol, 1.10 equiv) in THF (20 mL) was added sodium hydride (140 mg, 3.50 mmol, 5.00 equiv, 60% dispersion in mineral oil) at 0° C. The solution was stirred for 30 min at room temperature under nitrogen. Then tert-butyl N-(2-[4-chlorothieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (220 mg, 0.70 mmol, 1.00 equiv) in 5 mL of THF was added via syringe and the resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of brine and extracted with EtOAc. The organic layers were combined and dried over anhydrous sodium sulfate. After filtration and concentration in vacuo, the residue was purified by a silica gel column with DCM/MeOH (30:1-10:1) to provide 127 mg (39%) of tert-butyl N-[2-(4-[[4-(morpholin-4-yl)cyclohexyl]oxy]thieno[2,3-d]pyrimidin-6-yl)ethyl]carbamate as a white solid. MS (ES): m/z 463 (M+H)+.

Workup

  1. stirringthe resulting solution was stirred 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 in vacuo
  6. customthe residue was purified by a silica gel column with DCM/MeOH (30:1-10:1)

Sources & evidence

ORD record
ord-ef0e4af8081840f88648a81d6500de35
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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