Ethanol → 2-(5-Aminopyrazin-2-yl)ethanol

HRID 595880Notes

Reaction equation

HRID 595880 reaction equation
[CH2:1]([C:4]1[N:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)[CH:2]=C.[BH4-].[Na+].[NH4+].[Cl-].C([OH:17])C>C(Cl)Cl>[NH2:10][C:7]1[N:8]=[CH:9][C:4]([CH2:1][CH2:2][OH:17])=[N:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 218973655-Allylpyrazin-2-amine

Product 1

HCID 1180455072-(5-Aminopyrazin-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-allylpyrazin-2-amine (180 mg, 1.332 mmol) in DCM (26.6 mL) was cooled down to −78° C., then Ozone was bubbled through for 10 min until the solution turned to blue color. Then Nitrogen was purged through for 5 min. NaBH4 (151 mg, 4.00 mmol) in ethanol (10 mL) was added slowly, The reaction mixture was allowed to return to room temperature. After 1 h, Sat. NH4Cl was added slowly, the reaction mixture was then extracted by CHCl3/IPA (7:3) (3 times), the organic was dried and concentrated to yield the crude product. The crude product is used in next step reaction without purification. LCMS (m/z): 140.0 (MH+), 0.21 min.

Workup

  1. customOzone was bubbled through for 10 min until the solution
  2. customThen Nitrogen was purged through for 5 min
  3. customto return to room temperature
  4. extractionthe reaction mixture was then extracted by CHCl3/IPA (7:3) (3 times)
  5. customthe organic was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0489a042a5514108be4dfcd3bc14fdb1
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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