Hydrochloric Acid → HCID 23227007, compound

HRID 1956183Notes

Reaction equation

HRID 1956183 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH3:21][CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24].Cl[CH:29]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[F:44])[C:30]1[C:31]([S:36][CH3:37])=[N:32][CH:33]=[N:34][CH:35]=1.Cl>CCCCCC.O1CCCC1.CCOCC>[CH3:21][C:22]([CH3:27])([CH:29]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[F:44])[C:30]1[C:31]([S:36][CH3:37])=[N:32][CH:33]=[N:34][CH:35]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 11039Methyl isobutyrateHCID 2724682Lithium diisopropylamideHCID 23226983HCID 23226983, compoundHCID 178418339Butyllithium

Product 1

HCID 23227007HCID 23227007, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
12 °C

Procedure

To a solution of lithium diisopropylamide prepared from 5.3 g (57 mmol) of diisopropylamine and 21 mL (57 mmol) of 2.5M n-butyl lithium in hexane and 100 mL of dry tetrahydrofuran at -10° C. was slowly added with stirring 5.3 g (57 mmol) of methyl 2-methylpropanoate. The resulting solution was allowed to warm slowly to 12° C. and was then recooled to -10° C. To this was added in small portions with stirring 7.0 g (26 mmol) of 5-(chloro-(2-fluorophenyl)methyl)-4-methylthiopyrimidine. After 1 hr the resulting solution was warmed to ambient temperature. Ether and dilute aqueous hydrochloric acid were added and the ethereal phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 5.3 g (60 of theory) of the title compound as a colorless oil.

Workup

  1. additionwas slowly added
  2. customwas then recooled to -10° C
  3. additionTo this was added in small portions
  4. temperatureAfter 1 hr the resulting solution was warmed to ambient temperature
  5. customthe ethereal phase was recovered
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-befbf5c1f39c4e3299b46d5c6f9b4b1e
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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