Sodium hydride → HCID 86695236, compound

HRID 1504076Notes

Reaction equation

HRID 1504076 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:12])[C@H:5]1[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7][CH2:6]1.Cl[C:14]1[C:15]2[CH:22]=[C:21]([CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[S:20][C:16]=2[N:17]=[CH:18][N:19]=1>C1COCC1>[CH3:3][N:4]([CH3:12])[CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:14]2[C:15]3[CH:22]=[C:21]([CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86695235HCID 86695235, compoundHCID 178484116HCID 178484116, compound

Product 1

HCID 86695236HCID 86695236, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (80 mg, 2.00 mmol, 4.83 equiv, 60% dispersion in mineral oil) was treated with trans-4-(dimethylamino)cyclohexan-1-ol (80 mg, 0.56 mmol, 1.35 equiv) in 10 mL of distilled THF for 30 min at 0° C. under nitrogen. Then a solution of tert-butyl N-(2-[4-chlorothieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (130 mg, 0.41 mmol, 1.00 equiv) in 3 mL of THF was added and stirred at room temperature for 12 hours. After cooling to 0° C., the reaction was quenched with water and extracted with 3×30 mL of ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (4:1) to give 140 mg (80%) of tert-butyl N-[2-(4-[[4-(dimethylamino)cyclohexyl]oxy]thieno[2,3-d]pyrimidin-6-yl)ethyl]carbamate as a white solid. MS (ES): m/z 421 (M+H)+.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction was quenched with water
  3. extractionextracted with 3×30 mL of ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-39b85f890d1c4d52b648e3019fc92a8a
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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