Aluminium lithium hydride → HCID 178437737, compound

HRID 1458667Notes

Reaction equation

HRID 1458667 reaction equation
[CH2:1]([C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C@H:10]2[CH2:15][CH2:14][C@@H:13]([Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:11]2)[C:4]=1[C:20](OC)=[O:21])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C@H:10]2[CH2:15][CH2:14][C@@H:13]([Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:11]2)[C:4]=1[CH2:20][OH:21])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178437738HCID 178437738, compound

Product 1

HCID 178437737HCID 178437737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.0 g (20.9 mmol) of 5-methoxycarbonyl-6-ethyl-4-(cis-4-(trimethylsilyl)cyclohexylamino)pyrimidine (Example 6) in 30 ml of absolute tetrahydrofuran was added dropwise to a suspension, cooled to -30° C., of 1.03 g (27.1 mmol) of lithium aluminum hydride in 10 ml of absolute tetrahydrofuran, and the mixture was stirred at room temperature until the end of reaction. Following the hydrolysis, the mixture was subjected to extraction with diethyl ether to give, after drying and removal of the solvent, 6.13 g (19.9 mmol)=95% of the hydroxymethyl compound in the form of white crystals.

Workup

  1. customthe hydrolysis
  2. extractionthe mixture was subjected to extraction with diethyl ether
  3. customto give
  4. customafter drying
  5. customremoval of the solvent, 6.13 g (19.9 mmol)=95% of the hydroxymethyl compound in the form of white crystals

Sources & evidence

ORD record
ord-8c3003e7b17d46b6a38afd64de19f5fd
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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