Ethanol → 4-(3-chlorophenyl)-1-ethyl-7-hydroxymethylpyrido[2,3-d]pyrimidin-2(1H)-one

HRID 368986Notes

Reaction equation

HRID 368986 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[N:19][C:12]=3[N:13]([CH2:17][CH3:18])[C:14](=[O:16])[N:15]=2)[CH:7]=[CH:8][CH:9]=1.C(O)C>CC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[N:19][C:12]=3[N:13]([CH2:17][CH3:18])[C:14](=[O:16])[N:15]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 23284478HCID 23284478, compound

Product 1

HCID 232844794-(3-chlorophenyl)-1-ethyl-7-hydroxymethylpyrido[2,3-d]pyrimidin-2(1H)-oneYield 23.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium borohydride (35 mg, 0.9 mmol) was added to a mixture of 1.16 g (3.7 mmol) of 4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one-7-carbaldehyde and 20 ml of ethanol under ice-cooling, followed by stirring for 30 minutes under ice-cooling. The reaction solution was mixed with acetone and concentrated under a reduced pressure, and the resulting residue was mixed with water and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and the resulting filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate-chloroform) and further recrystallized from acetonitrile-ethanol to give 271 mg of 4-(3-chlorophenyl)-1-ethyl-7-hydroxymethylpyrido[2,3-d]pyrimidin-2(1H)-one. The yield was 23%.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationconcentrated under a reduced pressure
  4. additionthe resulting residue was mixed with water
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate, magnesium sulfate
  7. customwas removed by filtration
  8. concentrationthe resulting filtrate was concentrated under a reduced pressure
  9. customThereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate-chloroform)
  10. customfurther recrystallized from acetonitrile-ethanol

Sources & evidence

ORD record
ord-14aa2401b0754d1f9f290734cb79f15b
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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