Aluminium lithium hydride → 4-Amino-2-ethyl-5-pyrimidinemethanol

HRID 509446Notes

Reaction equation

HRID 509446 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[C:13]([C:14]([O-])=[O:15])=[CH:12][N:11]=[C:10]([CH2:17][CH3:18])[N:9]=1>C1COCC1>[NH2:7][C:8]1[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[C:10]([CH2:17][CH3:18])[N:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131733248HCID 131733248, compound

Product 1

HCID 202681494-Amino-2-ethyl-5-pyrimidinemethanolYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 100 ml flask equipped with constant pressure dropping funnel and drying pipe, 3.8 g (0.1 mol) of LiAlH4 and 20 ml of THF were charged, cooled with ice bath. 7.8 g (0.04 mol) of 4-amino-2-ethylpyrimidine-5-carboxylate in the 20 ml of THF was dropped into the flask slowly. After the addition was finished, the reaction was stirred for 1-2 h. The reaction was quenched with water and the solid was removed by filtration. The filtrate was concentrated. To the residue, 20 ml of ethyl acetate and 120 ml of petroleum ether were added. After shaking and standing, large amount of white solids precipitated. 4.59 g of aim product was obtained by filtration (yield 75%).

Workup

  1. customTo a 100 ml flask equipped with constant pressure
  2. additionwere charged
  3. temperaturecooled with ice bath
  4. additionAfter the addition
  5. customThe reaction was quenched with water
  6. customthe solid was removed by filtration
  7. concentrationThe filtrate was concentrated
  8. additionTo the residue, 20 ml of ethyl acetate and 120 ml of petroleum ether were added
  9. stirringAfter shaking
  10. customlarge amount of white solids precipitated
  11. custom4.59 g of aim product was obtained by filtration (yield 75%)

Sources & evidence

ORD record
ord-56d8d16a33c14de1a49d1d0df68dc7d4
Source dataset
uspto-grants-2015_08
Patent number
US09096581B2

Reaction notes

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