Water → HCID 58446794, compound

HRID 1958342Notes

Reaction equation

Br.[NH2:2][C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[C:10]([C:12]3[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=3)[N:11]=[C:5]2[N:4]=1.Br[CH2:20][CH2:21][F:22].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[F:22][CH2:21][CH2:20][O:18][C:14]1[CH:13]=[C:12]([C:10]2[N:11]=[C:5]3[N:4]=[C:3]([NH2:2])[CH:8]=[CH:7][N:6]3[CH:9]=2)[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

In a sealed tube 3-(7-aminoimidazo[1,2-a]pyrimidin-2-yl)phenol hydrobromide (800 mg, 2.6 mmol) was combined with DMF (4.0 ml) to give a light brown solution. 1-Bromo-2-fluoroethane (476 mg, 3.75 mmol) dissolved in DMF (4.0 ml) and Cs2CO3 (1.62 g, 4.97 mmol) were added. The reaction mixture was stirred 23 h at 70° C. H2O (50 ml) was added to the reaction mixture and the product was extracted with EtOAc (3×40 ml). After drying over MgSO4, filtration and concentration in vacuum, the crude product (orange oil) was purified by flash chromatography (50 g SiO2—NH2 cartridge, eluent: CH2Cl2 to CH2Cl2/MeOH 95:5) to yield the title compound (150 mg, 21%).

Workup

customto give a light brown solution
extractionthe product was extracted with EtOAc (3×40 ml)
dry with materialAfter drying over MgSO4, filtration and concentration in vacuum
customthe crude product (orange oil) was purified by flash chromatography (50 g SiO2—NH2 cartridge, eluent: CH2Cl2 to CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record: ord-af0849eac9e7469483847d0673f4dfdf
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410117B2

Reaction notes

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