Hydrochloric Acid → 2-(5-Bromopyrazin-2-yl)propan-2-ol

HRID 715536Notes

Reaction equation

HRID 715536 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5](C(OC)=O)=[N:6][CH:7]=1.[CH3:12][Mg]Br.C([O:17][CH2:18][CH3:19])C.Cl>O1CCCC1>[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:18]([OH:17])([CH3:19])[CH3:12])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 27282430Methyl 5-bromopyrazine-2-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 665203412-(5-Bromopyrazin-2-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-bromopyrazine-2-carboxylate (0.250 g, 1.152 mmol) in Tetrahydrofuran (THF) (6.53 ml) at 0° C. under nitrogen was added methylmagnesium bromide, 3 M in diethyl ether (1.152 ml, 3.46 mmol) slowly. After 1 hour at 0° C., 2N HCl (15 mL) was added slowly. The mixture was extracted with ethyl acetate (2×15 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. The residue was purified using silica gel chromatography CISCO): 10-30% ethyl acetate/hexanes (20 min), 12 gram silica gel column. Obtained 2-(5-bromopyrazin-2-yl)propan-2-ol as an orange oil (71 mg, 24%). MS (m/z) 216.9 (M+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×15 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. custom10-30% ethyl acetate/hexanes (20 min), 12 gram silica gel column

Sources & evidence

ORD record
ord-bd7156e34ae74f0bbc16f9eebedf0459
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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