Water → HCID 22386542, compound

HRID 1072416Notes

Reaction equation

HRID 1072416 reaction equation
[CH2:1]([S:3][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[C:6]([C:13]2[CH:14]=[C:15]([OH:20])[C:16](O)=[CH:17][CH:18]=2)[N:5]=1)[CH3:2].[CH2:21](Br)[CH3:22].[C:24]([O-:27])([O-])=O.[K+].[K+].O.[CH3:31]N(C=O)C>>[CH2:21]([O:20][C:15]1[CH:14]=[C:13]([C:6]2[N:5]=[C:4]([S:3][CH2:1][CH3:2])[N:9]3[CH:10]=[CH:11][N:12]=[C:8]3[CH:7]=2)[CH:18]=[CH:17][C:16]=1[O:27][CH2:24][CH3:31])[CH3:22]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 135556678HCID 135556678, compound

Product 1

HCID 22386542HCID 22386542, compoundYield 36%

Conditions

Temperature
50 °C

Procedure

To 4-(5-Ethylsulfanyl-imidazo[1,2-c]pyrimidin-7-yl)-benzene-1,2-diol (86.2 mg, 0.3 mmol) in DMF (2 ml) were added ethyl bromide (112 μl, 1.5 mmol) and K2CO3 (290 mg, 2.1 mmol). The reaction mixture was stirred at about 50° C. overnight. After cooling to room temperature, it was poured into water and extracted with EtOAc. The combined organic extract was dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography to give 7-(3,4-Diethoxy-phenyl)-5-ethylsulfanyl-imidazo[1,2-c]pyrimidine (39.1 mg, yield 36%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe combined organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-3466614857ef4df69b05df68f51af4ca
Source dataset
uspto-grants-2005_06
Patent number
US06911443B2

Reaction notes

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