Water → HCID 118308754, compound

HRID 923473Notes

Reaction equation

HRID 923473 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]([C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:14])[C:9](OCC)=[O:10].O.[OH-].[Na+]>C1COCC1>[NH2:7][C:8]([C:15]1[N:16]=[CH:17][CH:18]=[CH:19][N:20]=1)([CH3:14])[CH2:9][OH:10]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 118308756HCID 118308756, compound

Product 1

HCID 118308754HCID 118308754, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4 mg of lithium aluminum hydride and 0.2 ml of THF was added dropwise a solution of 20 mg of ethyl 2-amino-2-(pyrimidin-2-yl)propanoate in 0.2 ml of THF at 0° C. solution, followed by stirring at the same temperature for 7 hours. 2.5 mg of lithium aluminum hydride was added thereto, followed by stirring at 0° C. for 1 hour. 32 μl of water, 32 μl of a 15% aqueous sodium hydroxide solution, and 96 μl of water were sequentially added thereto at 0° C. The insoluble materials of the reaction mixture were filtered over Celite and washed with ethyl acetate, and the filtrate was then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 7 mg of 2-amino-2-(pyrimidin-2-yl)propan-1-ol.

Workup

  1. stirringby stirring at 0° C. for 1 hour
  2. customat 0° C
  3. filtrationThe insoluble materials of the reaction mixture were filtered over Celite
  4. washwashed with ethyl acetate
  5. concentrationthe filtrate was then concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cde3126d18d847629b82c9504d3300ce
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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