Water → HCID 178467458, compound

HRID 1458662Notes

Reaction equation

HRID 1458662 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH:11]([C:13]1[N:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]2[CH2:25][CH2:24][C@@H:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]2)[C:14]=1[Cl:30])[CH3:12])(=O)C.O>O1CCCC1>[C:26]([C@@H:23]1[CH2:22][CH2:21][C@H:20]([NH:19][C:15]2[C:14]([Cl:30])=[C:13]([CH:11]([OH:10])[CH3:12])[N:18]=[CH:17][N:16]=2)[CH2:25][CH2:24]1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178476202HCID 178476202, compound

Product 1

HCID 178467458HCID 178467458, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.5 g (40 mmol) of lithium aluminum hydride were placed in 100 ml of dry tetrahydrofuran, and a solution of 14 g (40 mmol) of 6-(1-acetoxyethyl)-4-(cis-4-tert-butylcyclohexylamino)-5-chloropyrimidine (Example 30) in 50 ml of dry tetrahydrofuran was added dropwise at a temperature of 20° to 30° C. The mixture was then heated at reflux for 2 hours. After cooling, 5 ml of water were added carefully dropwise and, after standing overnight, the mixture was filtered with suction to remove the inorganic material. The filtrate was concentrated and the residue was chromatographed on silica gel (ethyl acetate/methanol 9:1) to give 6.0 g (48.1% of theory) of a colorless oil.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered with suction
  5. customto remove the inorganic material
  6. concentrationThe filtrate was concentrated
  7. customthe residue was chromatographed on silica gel (ethyl acetate/methanol 9:1)
  8. customto give 6.0 g (48.1% of theory) of a colorless oil

Sources & evidence

ORD record
ord-d2177e0fadce4c7dbb0314037430fce4
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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