Chloride → HCID 118045610, compound

HRID 595854Notes

Reaction equation

HRID 595854 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=2)=[N:6][CH:7]=1.[Ce].[Cl-].[BH4-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)C.O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH:9]=2)=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 312ChlorideHCID 23974CeriumHCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 118045873HCID 118045873, compound

Product 1

HCID 118045610HCID 118045610, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(5-aminopyrazin-2-yl)cyclohex-2-enone (150 mg, 0.793 mmol) in ethanol (2643 μL) was added cerium (Ill) chloride (293 mg, 1.189 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 h until all the materials were dissolved. The reaction mixture was then cooled to 0° C. and sodium borohydride (45.0 mg, 1.189 mmol) was added in portions. The reaction mixture was stirred upon warming up to room temperature for 2 h. The reaction mixture was cooled to 0° C. and 2 mL of water was slowly added until the bubbles clearly showed up and then disappeared, Continued to stir for 30 min. Then, sodium sulfate was added and stirred for 30 min. Filtered and dried under high vacuum to provide 149 mg of desired product. LCMS (m/z): 192.1 (MH+), 0.46 min.

Workup

  1. dissolutionwere dissolved
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. stirringThe reaction mixture was stirred
  4. temperatureupon warming up to room temperature for 2 h
  5. temperatureThe reaction mixture was cooled to 0° C.
  6. stirringContinued to stir for 30 min
  7. stirringstirred for 30 min
  8. filtrationFiltered
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-ba9fe17ec4254065afd718ac8a0d03ec
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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