Sodium borohydride → HCID 178498838, compound

HRID 862711Notes

Reaction equation

HRID 862711 reaction equation
[BH4-].[Na+].[OH-].[CH3:4][N+:5]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[N:7][C:6]=1[NH:15][CH2:16][C:17]1[CH:26]=[CH:25][C:22]([O:23][CH3:24])=[C:19]([O:20][CH3:21])[CH:18]=1>C(O)C>[CH3:4][N:5]1[CH2:10][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][N:7]=[C:6]1[NH:15][CH2:16][C:17]1[CH:26]=[CH:25][C:22]([O:23][CH3:24])=[C:19]([O:20][CH3:21])[CH:18]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19698828HCID 19698828, compound

Product 1

HCID 178498838HCID 178498838, compoundYield 122.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.170 g (3 eq) of sodium borohydride is added to 0.400 g of 1-methyl-2-veratrylamino-5-methoxycarbonylpyrimidiniumhydroxide dissolved in 50 ml of ethanol. The mixture is stirred under argon at room temperature for three hours. After evaporation of the ethanol, the medium is extracted with dichloromethane and water. The organic phases are washed with a saturated sodium chloride solution and then dried over sodium sulfate. The oil resulting from evaporation of the organic phases, purified on silica gel under medium pressure (eluent: 15% MeOH/CH2 Cl2) gives 467 mg (yield: 98%) of the corresponding 1,6-dihydropyrimidine.

Workup

  1. customAfter evaporation of the ethanol
  2. extractionthe medium is extracted with dichloromethane and water
  3. washThe organic phases are washed with a saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe oil resulting from evaporation of the organic phases
  6. custompurified on silica gel under medium pressure (eluent: 15% MeOH/CH2 Cl2)

Sources & evidence

ORD record
ord-d8db8d0762a64d59a9d702c73a6d5a03
Source dataset
uspto-grants-1998_02
Patent number
US05719187

Reaction notes

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