Acetonitrile → HCID 57406939, compound

HRID 2408345Notes

Reaction equation

HRID 2408345 reaction equation
Cl[C:2]1[N:3]=[C:4]2[NH:13][C@H:12]([C:14]([F:17])([F:16])[F:15])[CH2:11][CH2:10][N:5]2[C:6](=[O:9])[C:7]=1[F:8].C1(C)C=CC(S(O[CH2:28][CH2:29][O:30][CH:31]([CH3:33])[CH3:32])(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:41]([O:44][CH2:45][CH3:46])(=O)[CH3:42].C(#[N:49])C>>[F:8][C:7]1[C:6](=[O:9])[N:5]2[CH2:10][CH2:11][C@@H:12]([C:14]([F:17])([F:16])[F:15])[N:13]([CH2:28][CH2:29][O:30][CH:31]([CH3:32])[CH3:33])[C:4]2=[N:3][C:2]=1[N:49]1[CH2:46][CH2:45][O:44][CH2:41][CH2:42]1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 190994432-Isopropoxyethyl 4-methylbenzenesulfonateHCID 136350279HCID 136350279, compound

Product 1

HCID 57406939HCID 57406939, compound

Conditions

Temperature
100 °C

Procedure

To 0.15 g (0.552 mmol) of (8S)-2-chloro-3-fluoro-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one, in solution in 3 cm3 of acetonitrile, are added at a temperature close to 20° C., 0.157 g (0.607 mmol) of 2-isopropoxy-ethyl toluene-4-sulfonate and 0.2 g (0.607 mmol) of cesium carbonate. After 1 hour of stirring at 100° C. in a microwave appliance, the reaction medium is poured into 25 cm3 of ethyl acetate and then washed twice with 10 cm3 of distilled water. The organic phase is dried on anhydrous magnesium sulfate, filtered and dry concentrated under reduced pressure (2.7 kPa) in order to obtain 0.254 g of a residue. This residue is purified by flash chromatography on silica [eluent: cyclohexane/ethyl acetate (8/2 by volume)]. After concentration of the fractions under reduced pressure (2.7 kPa), 0.86 g of (8S)-2-chloro-3-fluoro-9-(2-isopropoxy-ethyl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]-pyrimidin-4-one are obtained as a colorless oil including the following characteristics:

Workup

  1. customclose to 20° C.
  2. washwashed twice with 10 cm3 of distilled water
  3. dry with materialThe organic phase is dried on anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customdry
  6. concentrationconcentrated under reduced pressure (2.7 kPa) in order

Sources & evidence

ORD record
ord-91b09a48053f45c089160372f11c4b1a
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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