Water → HCID 178437735, compound

HRID 1419798Notes

Reaction equation

HRID 1419798 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][C@@H:11]2[CH2:16][CH2:15][C@H:14]([C:17](OCC)=[O:18])[CH2:13][CH2:12]2)=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Cl:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][C@@H:14]([CH2:17][OH:18])[CH2:13][CH2:12]2)=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178472432HCID 178472432, compound

Product 1

HCID 178437735HCID 178437735, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 12.47 g (0.040 mol) of ethyl cis-4-(5-chloro-6-ethylpyrimidin-4-ylamino)-cyclohexanecarboxylate (preparation: DE-A-44 17 163) in 25 ml of dry tetrahydrofuran was added dropwise at from 20° to 30° C. to a suspension of 1.52 g (0.04 mol) of lithium aluminum hydride in 150 ml of dry tetrahydrofuran. The mixture was subsequently stirred at 50° C. for 1 hour and cooled to room temperature, and 10 ml of water were carefully added dropwise. After removal of inorganic material by filtration with suction, the organic phase was dried and concentrated. For purification, the crude product was chromatographed on silica gel (using ethyl acetate as eluent). 5.2 g (48.2% of theory) were obtained of a yellow oil which solidified on standing. m.p.: 71° to 72° C.

Workup

  1. temperaturecooled to room temperature
  2. customAfter removal of inorganic material
  3. filtrationby filtration with suction
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. customFor purification
  7. customthe crude product was chromatographed on silica gel (using ethyl acetate as eluent)
  8. custom5.2 g (48.2% of theory) were obtained of a yellow oil which

Sources & evidence

ORD record
ord-2857e551436f4ff1a26c4efd0c71f4c2
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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