2-Amino-3,5-dibromopyrazine → 6-Bromo-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine

HRID 1623385Notes

Reaction equation

HRID 1623385 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[O:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1>CC#N>[Br:8][C:6]1[N:7]=[C:2]([NH:17][CH2:16][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)[C:3]([NH2:9])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 6200042-Amino-3,5-dibromopyrazineHCID 27732104-Aminomethyltetrahydropyran

Product 1

HCID 866263946-Bromo-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamineYield 61.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a scintillation vial containing 3,5-dibromopyrazin-2-amine (500 mg, 1.977 mmol) and TEA (0.551 ml, 3.95 mmol) was added MeCN (6 ml) and (tetrahydro-2H-pyran-4-yl)methanamine (300 mg, 1.977 mmol). The homogenous reaction mixture was capped and heated to 80° C. in a oil bath for 36 hr. The reaction mixture was concentrated to dryness, diluted with EtOAc and washed with sat NaHCO3, sat NaCl. The organic layer was dried Na2SO4, filtered and concentrated. The crude was purified by column chromatography on silica gel (30% EtOAc/Hexane) to yield 6-bromo-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine (351 mg, 1.222 mmol, 61.8% yield).

Workup

  1. customThe homogenous reaction mixture was capped
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additiondiluted with EtOAc
  4. washwashed
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by column chromatography on silica gel (30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-baeeee39d1bc49d398f0406660ebdbc0
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

Loading…