Sodium borohydride → HCID 11695520, compound

HRID 743074Notes

Reaction equation

HRID 743074 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][N:6]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(C(Cl)(Cl)Cl)[C:10]2[CH:22]=[CH:23][CH:24]=[N:25][C:9]=2[NH:8][C:7]1=[O:26])[CH3:2].[BH4-].[Na+]>CN(C)C=O>[CH2:27]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:22]=[CH:23][CH:24]=[N:25][C:9]=2[NH:8][C:7]1=[O:26])[CH3:28]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11676583HCID 11676583, compound

Product 1

HCID 11695520HCID 11695520, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 240 mg (0.54 mmol) of 3-[2(diethylamino)ethyl]-4-phenyl-4-trichloromethyl-2-oxo -1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine in 10 mL of dimethylformamide was added 82 mg (1.26 mmol) of sodium borohydride at temperature of 5° C. to 15° C. After being stirred for 3 hours at ambient temperature, the reaction mixture was poured onto ice water, and the mixture was extracted with ethyl acetate. The organic layer separated was washed with water and then with brine, dried on anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform) to give 110 mg (0.34 mmol) of the title compound.

Workup

  1. additionthe reaction mixture was poured onto ice water
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer separated
  4. washwas washed with water
  5. dry with materialwith brine, dried on anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform)

Sources & evidence

ORD record
ord-a694f970e4c74302b2a1aeb80d137fd7
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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