3-Thiophenecarboxaldehyde → HCID 19423540, compound

HRID 743080Notes

Reaction equation

HRID 743080 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]3[CH:19]=[N:20][CH:21]=[CH:22][C:10]=3[NH:9][C:8]2=[O:23])[CH2:3][CH2:2]1.Cl.C(O)C.[S:28]1[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29]1.C([BH3-])#N.[Na+]>CO>[S:28]1[CH:32]=[CH:31][C:30]([CH2:33][N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[CH:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:11]4[CH:19]=[N:20][CH:21]=[CH:22][C:10]=4[NH:9][C:8]3=[O:23])[CH2:5][CH2:6]2)=[CH:29]1

Participants

6

Reactant 4

HCID 681353-ThiophenecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19423601HCID 19423601, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 19423540HCID 19423540, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 500 mg (1.62 mmol) of 3-(piperidin-4-yl)-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrido[4,3-d]pyrimidine in 30 mL of methanol were added 1,200 mg of 10% HCl/ethanol solution, 727 mg (6.48 mmol) of 3-thiophenecarboxaldehyde and 407 mg (6.48 mmol) of sodium cyanoborohydride under ice-cooling, and the mixture was stirred for 10 hours at ambient temperature. Then, the reaction mixture was concentrated in vacuo, and water was added to the residue. The mixture was adjusted to pH 10 and extracted with chloroform. The organic layer separated was dried on potassium carbonate, and then concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform) to give 550 mg (1.36 mmol) of the title compound.

Workup

  1. temperaturecooling
  2. concentrationThen, the reaction mixture was concentrated in vacuo, and water
  3. additionwas added to the residue
  4. extractionextracted with chloroform
  5. customThe organic layer separated
  6. customwas dried on potassium carbonate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform)

Sources & evidence

ORD record
ord-8cb4df1b4eec469592f85fb925a0f28c
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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