Methane → HCID 178517391, compound

HRID 1071957Notes

Reaction equation

HRID 1071957 reaction equation
[CH:1]1([NH:5][C:6]2[C:11](Br)=[N:10][C:9]([Br:13])=[CH:8][N:7]=2)[CH2:4][CH2:3][CH2:2]1.[OH-:14].[K+].C>O>[Br:13][C:9]1[N:10]=[C:11]([OH:14])[C:6]([NH:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 14797Potassium HydroxideHCID 21927739HCID 21927739, compound

Product 1

HCID 178517391HCID 178517391, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 2-(N-cyclobutylamino)-3,5-dibromopyrazine (EX-15B) (25.03 g, 81.53 mmol) in 500.0 mL water (0.16 M) was added potassium hydroxide (22.90 g, 408.1 mmol) in 480.0 mL water. The resulting suspension was heated to reflux for approximately 18 hours. The reaction mixture was then added charcoal and refluxed for an additional 15 minutes. The mixture was then allowed to cool for 5 minutes and was filtered through Celite 545. The filtrate was cooled in an ice bath and was acidified to a pH of approximately 5 (litmus paper) upon which a white precipitate forms. The precipitate was collected by filtration, washed twice with water, and dried under vacuum to afford pure 5-bromo-2-(N-cyclobutylamino)-3-hydroxypyrazine (EX-115C) in 80% yield: 1H NMR (400 MHz, DMSO) δ 12.43 (s, 1H), 7.18 (br d, J=5.1 Hz, 1H), 6.87 (s, 1H), 4.29-4.19 (m, 1H), 2.16-2.09 (m, 2H), 2.03-1.93 (m, 2H), 1.63-1.51 (m, 2H); 13C NMR (100 MHz, DMSO) δ 147.0, 144.2, 119.9, 41.3, 26.0, 10.8; HRMS (EI) calcd for C8H11BrN3O 244.0085, found 244.0086.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for approximately 18 hours
  3. temperatureto cool for 5 minutes
  4. filtrationwas filtered through Celite 545
  5. temperatureThe filtrate was cooled in an ice bath
  6. filtrationThe precipitate was collected by filtration
  7. washwashed twice with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-d3de5465887a4353b9e990aa94c912a2
Source dataset
uspto-grants-2005_06
Patent number
US06908919B2

Reaction notes

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