Cesium carbonate → HCID 58532508, compound

HRID 1846274Notes

Reaction equation

HRID 1846274 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:16](=[O:17])[C:15]3[CH:18]=[N:19][CH:20]=[CH:21][C:14]=3[N:13]=[C:12]2[C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([OH:29])=[C:24]([CH3:30])[CH:23]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:38][CH2:39][O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42]>CN(C=O)C.O>[C:44]([Si:41]([CH3:43])([CH3:42])[O:40][CH2:39][CH2:38][O:29][C:25]1[C:26]([CH3:28])=[CH:27][C:22]([C:12]2[N:11]([C:8]3[CH:9]=[CH:10][C:5]([CH:1]([CH2:3][CH3:4])[CH3:2])=[CH:6][CH:7]=3)[C:16](=[O:17])[C:15]3[CH:18]=[N:19][CH:20]=[CH:21][C:14]=3[N:13]=2)=[CH:23][C:24]=1[CH3:30])([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 136053080HCID 136053080, compound

Product 1

HCID 58532508HCID 58532508, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-sec-butyl-phenyl)-2-(4-hydroxy-3,5-dimethyl-phenyl)-3H-pyrido[4,3-d]pyrimidin-4-one (0.25 g, 0.63 mmol) in anhydrous DMF (10 mL) was added cesium carbonate (0.62 g, 1.9 mmol). The color changed to orange. The reaction mixture was stirred at room temperature for 10 minutes under nitrogen. Then, (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (9) (0.300 g, 1.27 mmol) was added and the reaction mixture was stirred at 80° C. for 5 hours under nitrogen, cooled to room temperature, diluted with water (100 mL), and extracted with ethyl acetate (100 mL). The organic phase was washed with water (2×50 mL), then brine (50 mL), and dried over anhydrous Na2SO4. The solvent was evaporated. The crude compound was purified by the Simpliflash system (30% ethyl acetate in hexanes as eluent) to give 2-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,5-dimethyl-phenyl}-3-(4-sec-butyl-phenyl)-3H-pyrido[4,3-d]pyrimidin-4-one (10) as a gummy solid. Yield: 0.20 g (58%).

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 5 hours under nitrogen
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe organic phase was washed with water (2×50 mL)
  5. dry with materialbrine (50 mL), and dried over anhydrous Na2SO4
  6. customThe solvent was evaporated
  7. customThe crude compound was purified by the Simpliflash system (30% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-aa85d6c6861a49ac9c08c1dc399a739d
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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