2-Bromo-1,1-dimethoxyethane → HCID 67458003, compound

HRID 1852964Notes

Reaction equation

HRID 1852964 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([S:14][CH2:15][CH3:16])[N:11]=[C:10]([NH2:17])[CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:19][CH:20](OC)OC>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([S:14][CH2:15][CH3:16])[N:11]3[CH:19]=[CH:20][N:17]=[C:10]3[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 67451926HCID 67451926, compound

Product 1

HCID 67458003HCID 67458003, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 6-(4-bromophenyl)-2-(ethylthio)pyrimidin-4-amine (35.00 g, 112.8 mmol) in 20 mL of THF and 200 mL of water was added 2-bromo-1,1-dimethoxyethane (38.14 g, 225.7 mmol) at ambient temperature. The reaction flask was fitted with a condenser and the mixture was allowed to proceed with stirring at reflux overnight. After 24 hours, the reaction mixture was cooled and poured into 400 mL of water. The solid was collected by vacuum filtration. The wet solid was suspended in 500 mL of aqueous saturated sodium bicarbonate and gas evolution was observed. The mixture was stirred at ambient temperature for 10 minutes before it was extracted with DCM (8×500 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude was then dried under high vacuum overnight to afford 7-(4-bromophenyl)-5-(ethylthio)imidazo[1,2-c]pyrimidine (31 g, 87.18 mmol, 77.27% yield). MS (apci) m/z=334.0 (M+H).

Workup

  1. customThe reaction flask was fitted with a condenser
  2. temperatureat reflux overnight
  3. temperaturethe reaction mixture was cooled
  4. filtrationThe solid was collected by vacuum filtration
  5. stirringThe mixture was stirred at ambient temperature for 10 minutes before it
  6. extractionwas extracted with DCM (8×500 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude was then dried under high vacuum overnight

Sources & evidence

ORD record
ord-2ceb7e5141254385b85dcc471664130b
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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