Sodium hydride → HCID 68041347, compound

HRID 1958048Notes

Reaction equation

HRID 1958048 reaction equation
[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[S:17][C:13]=3[C:12](=[O:24])[NH:11][C:10]2=[S:25])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>CN(C)C=O>[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[S:17][C:13]=3[C:12](=[O:24])[N:11]=[C:10]2[S:25][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 70695469HCID 70695469, compound

Product 1

HCID 68041347HCID 68041347, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-thioxo-5,6-dihydro[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (Example 107) (150 mg, 0.367 mmol) in N,N-Dimethylformamide (DMF) (2 mL) in a 20 mL Scintillation vial stirred at rt was added sodium hydride (27.8 mg, 1.100 mmol). After stirring at rt for 10 minutes, 1,1-dimethylethyl bromoacetate (0.108 mL, 0.734 mmol) was added and the reaction mixture was capped. Upon addition a precipitate immediately formed and the reaction mixture became a thick almost solid suspension. A portion of the solid was checked by LC/MS and it indicated that the reaction had gone about 80%. The reaction mixture was quenched with saturated NH4Cl solution and diluted with 15 mL water. The yellow-orange solid was isolated by filtration, washed with water and dried in a vacuum oven at 65 C for two hours providing 182 mg of solid that was used without further purification in the next step LC/MS (ES) m/z=524 (M+H).

Workup

  1. customthe reaction mixture was capped
  2. additionUpon addition a precipitate
  3. customimmediately formed
  4. customThe reaction mixture was quenched with saturated NH4Cl solution
  5. additiondiluted with 15 mL water
  6. customThe yellow-orange solid was isolated by filtration
  7. washwashed with water
  8. customdried in a vacuum oven at 65 C for two hours

Sources & evidence

ORD record
ord-1c0f2ca73aa044de901fd2d769bda738
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

Loading…