Hydrochloric Acid → 8-(2-(4-isopropyl-1,3-thiazol-2-yl)-ethyl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde

HRID 1828533Notes

Reaction equation

HRID 1828533 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][N:14]3[C:15](=[O:23])[C:16]([C:19](OC)=[O:20])=[CH:17][N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[H-].C([Al+]C(C)C)(C)C.[Cl-].[NH4+].Cl>O1CCCC1>[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][N:14]3[C:15](=[O:23])[C:16]([CH:19]=[O:20])=[CH:17][N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21896610Diisopropylaluminium hydrideHCID 22063631Methyl 8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-carboxylate2×

Product 1

HCID 220636238-(2-(4-isopropyl-1,3-thiazol-2-yl)-ethyl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehydeYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The methyl 8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-carboxylate (660 mg) obtained in (A) was dissolved in tetrahydrofuran (30 ml), added dropwise with diisopropylaluminum hydride (1 M solution in tetrahydrofuran, 9.2 ml) at −78° C., and then the mixture was stirred for 2 hours at the same temperature. The reaction mixture was added with saturated aqueous ammonium chloride (1 ml), then added with 12% aqueous hydrochloric acid, and stirred at room temperature for 1 hour. After insoluble solids were removed by filtration through a Celite layer, the solvent of the filtrate was evaporated, and the residue was dissolved in methylene chloride. This solution was added with active manganese dioxide (1.2 g) and stirred at room temperature for 16 hours. Then, insoluble matters were removed by filtration to obtain the title compound (390 mg) as yellow powder.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customAfter insoluble solids were removed by filtration through a Celite layer
  3. customthe solvent of the filtrate was evaporated
  4. dissolutionthe residue was dissolved in methylene chloride
  5. additionThis solution was added with active manganese dioxide (1.2 g)
  6. stirringstirred at room temperature for 16 hours
  7. customThen, insoluble matters were removed by filtration

Sources & evidence

ORD record
ord-f6c7e822940a4d2fa45436091f65aaf3
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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