Aluminium lithium hydride → HCID 66760787, compound

HRID 1188707Notes

Reaction equation

HRID 1188707 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH:12][C:13]1[C:18]([C:19]([O-])=[O:20])=[CH:17][N:16]=[C:15]([S:22][CH3:23])[N:14]=1)[CH2:9][CH2:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH:12][C:13]1[C:18]([CH2:19][OH:20])=[CH:17][N:16]=[C:15]([S:22][CH3:23])[N:14]=1)[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86662392HCID 86662392, compound

Product 1

HCID 66760787HCID 66760787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(7-methoxy-2,3-dihydro-1H-inden-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate (3.25 g, 9.04 mmol) in anhydrous tetrahydrofuran (30 mL) was added dropwise to a suspension of lithium aluminum hydride (0.54 g, 14.25 mmol) in anhydrous tetrahydrofuran (8 mL) at 0-5° C. The reaction mixture was allowed to slowly warm to room temperature and stirred for 18 h, then the mixture was cooled to 0-5° C. and quenched with water:tetrahydrofuran (15 mL:5 mL), followed by a 10% sodium hydroxide solution (11 mL). After stirring for 1 h, the precipitate was filtered off and washed with ethyl acetate (5×25 mL). The combined filtrates were diluted with saturated brine solution (20 mL) and water (15 mL), the two phases were separated, and the organic layer was washed with water (1×25 mL), dried over magnesium sulfate, filtered and evaporated to a light brown solid (2.43 g, 7.65 mmol, 84%). ESMS m/z 318 (M+H)+.

Workup

  1. temperaturethe mixture was cooled to 0-5° C.
  2. customquenched with water
  3. stirringAfter stirring for 1 h
  4. filtrationthe precipitate was filtered off
  5. washwashed with ethyl acetate (5×25 mL)
  6. additionThe combined filtrates were diluted with saturated brine solution (20 mL) and water (15 mL)
  7. customthe two phases were separated
  8. washthe organic layer was washed with water (1×25 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-92b1d520c6d946589ed0102de5a11f22
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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