Sodium borohydride → HCID 58200236, compound

HRID 539647Notes

Reaction equation

HRID 539647 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[NH:12][C:13]1[N:17]2[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:19][N:20]=[CH:21][C:16]2=[N:15][N:14]=1.[BH4-].[Na+]>C1COCC1.C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[NH:12][C:13]1[N:17]2[CH:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:19][NH:20][CH2:21][C:16]2=[N:15][N:14]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58200290HCID 58200290, compound

Product 1

HCID 58200236HCID 58200236, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring suspension of (2-bromo-4,5-dimethoxy-phenyl)-(5-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-amine (0.2 g, 3.7 mmol) in a mixture of THF (20 mL) and TFA (1 mL) at 0° C. was added sodium borohydride (20 mg, 4.0 mmol). The reaction mixture was stirred 15 minutes at room temperature, thane quenched by addition of 10% aqueous HCl. The resulting mixture was heated to reflux for 10 minutes, then cooled and made basic by addition of 1M aqueous NaOH. The mixture was extracted with EtOAc, and the combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure to give 0.18 g of (2-bromo-4,5-dimethoxy-phenyl)-(5-phenyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-amine, MS (M+H)=431.

Workup

  1. customthane quenched by addition of 10% aqueous HCl
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 10 minutes
  4. temperaturecooled
  5. additionmade basic by addition of 1M aqueous NaOH
  6. extractionThe mixture was extracted with EtOAc
  7. dry with materialthe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a14f3c02db594a4e8949614ac37b781a
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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