Water → 5-Bromo-3-cyclobutylmethoxy-pyrazin-2-ylamine

HRID 639298Notes

Reaction equation

HRID 639298 reaction equation
[H-].[Na+].[CH:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1.[NH2:9][C:10]1[C:15](Br)=[N:14][C:13]([Br:17])=[CH:12][N:11]=1.O>O1CCCC1>[Br:17][C:13]1[N:14]=[C:15]([O:8][CH2:7][CH:3]2[CH2:6][CH2:5][CH2:4]2)[C:10]([NH2:9])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 78130CyclobutylcarbinolHCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 866195175-Bromo-3-cyclobutylmethoxy-pyrazin-2-ylamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.96 g, 23.7 mmol) was added in portions to a solution of cyclobutanemethanol (2.2 mL, 23.7 mmol) in tetrahydrofuran (30 mL) at 0° C., the reaction mixture was stirred at room temperature for 45 minutes. A solution of 2-amino-3,5-dibromopyrazine (3.0 g, 11.9 mmol) in tetrahydrofuran (10 mL) was added and the reaction mixture was heated at 50° C. for 16 hours. The reaction mixture was cooled to room temperature and water (2 mL) was added, the whole was then concentrated in vacuo to give a brown oil. The crude product was purified by flash column chromatography (100% dichloromethane) to give 5-bromo-3-cyclobutylmethoxy-pyrazin-2-ylamine as a pale yellow solid, 3.19 g (100% yield). LC@215 nm; Rt 2.11: 93%, m/z (ES+): 259 (M+H).

Workup

  1. temperaturethe reaction mixture was heated at 50° C. for 16 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationthe whole was then concentrated in vacuo
  4. customto give a brown oil
  5. customThe crude product was purified by flash column chromatography (100% dichloromethane)

Sources & evidence

ORD record
ord-2d7d3695021141bc9bce493e65ffed47
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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