Cesium carbonate → HCID 57389530, compound

HRID 2408333Notes

Reaction equation

HRID 2408333 reaction equation
[CH3:1][C@@:2]1([C:18]([F:21])([F:20])[F:19])[CH2:17][N:5]2[C:6](=[O:16])[CH:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[N:9]=[C:4]2[NH:3]1.[CH3:22][C:23]1([O:26][CH2:25]1)[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[OH:26][C:23]([CH3:25])([CH3:24])[CH2:22][N:3]1[C:4]2=[N:9][C:8]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)=[CH:7][C:6](=[O:16])[N:5]2[CH2:17][C@@:2]1([CH3:1])[C:18]([F:21])([F:19])[F:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11208Isobutylene oxideHCID 136069602(2S)-2-methyl-7-morpholin-4-yl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Product 1

HCID 57389530HCID 57389530, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

To 0.500 g (1.643 mmol) of (S)-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one, in solution in 15 cm3 of acetonitrile, are added at a temperature close to 20° C., 1.185 g (16.43 mmol) of isobutylene oxide and 0.535 g (16.43 mmol) of cesium carbonate. After 1 hour of stirring at 120° C. and 1 hour 30 mins at 130° C. in a microwave appliance, the reaction medium is dry concentrated under reduced pressure (2.7 kPa) and then diluted in 30 cm3 of ethyl acetate and then washed with twice 20 cm3 of distilled water and 30 cm3 of solution saturated with sodium chloride. The organic phase is dried on anhydrous magnesium sulfate, filtered and dry concentrated under reduced pressure (2.7 kPa) in order to obtain a pale yellow oil which is purified by flash chromatography on silica [eluent: dichloromethane/methanol/acetonitrile (94/3/3 by volume)]. After concentration of the fractions under reduced pressure (2.7 kPa), 500 mg of (S)-1-(2-hydroxy-2-methyl-propyl)-2-methyl-7-(morpholin-4-yl)-2-(trifluoro-methyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one are obtained as a white solid melting at 72° C. and including the following characteristics:

Workup

  1. customclose to 20° C.
  2. customthe reaction medium is dry
  3. concentrationconcentrated under reduced pressure (2.7 kPa)
  4. additiondiluted in 30 cm3 of ethyl acetate
  5. washwashed with twice 20 cm3 of distilled water and 30 cm3 of solution saturated with sodium chloride
  6. dry with materialThe organic phase is dried on anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customdry
  9. concentrationconcentrated under reduced pressure (2.7 kPa) in order
  10. customto obtain a pale yellow oil which
  11. customis purified by flash chromatography on silica [eluent: dichloromethane/methanol/acetonitrile (94/3/3 by volume)]

Sources & evidence

ORD record
ord-955e0d6fae904daf853151d7ca34f1ba
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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