Water → HCID 21873962, compound

HRID 723416Notes

Reaction equation

HRID 723416 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]2[C:12]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=[CH:9][N:8]2[C:20]=1[CH3:21])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:2][CH2:3][C:5]1[N:6]=[C:7]2[C:12]([NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])=[CH:11][CH:10]=[CH:9][N:8]2[C:20]=1[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21873922HCID 21873922, compound

Product 1

HCID 21873962HCID 21873962, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 36.6 g of 2-methoxycarbonyl-3-methyl-8-pivaloylaminoimidazo[1,2-a]pyridine in 400 ml of dry tetrahydrofuran are added 5.5 g of lithium aluminium hydride at ambient temperature over a period of 1 h. The reaction mixture is then carefully hydrolysed with 15 ml water and 16 ml 15% sodium hydroxide solution. The precipitate is removed by filtration and washed thoroughly with tetrahydrofuran. The filtrate is washed with 100 ml saturated ammonium chloride solution and concentrated in vacuo. The residue is dissolved in 400 ml tetrahydrofuran/toluene 1:1 (v/v) and the solvent distilled off at 80° C. The precipitate is filtered off and dried in vacuo to yield 27.2 g (83%) of the title compound (m.p. 186–187° C.).

Workup

  1. customThe precipitate is removed by filtration
  2. washwashed thoroughly with tetrahydrofuran
  3. washThe filtrate is washed with 100 ml saturated ammonium chloride solution
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in 400 ml tetrahydrofuran/toluene 1:1 (v/v)
  6. distillationthe solvent distilled off at 80° C
  7. filtrationThe precipitate is filtered off
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e0cd5cb67abd40c6ab8bf851defd3752
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

Loading…