Hydrochloric Acid → HCID 178446219, compound

HRID 1817047Notes

Reaction equation

HRID 1817047 reaction equation
Br[C:2]1[N:3]=[C:4]2[N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:9](=[O:16])[N:8](C(OC(C)(C)C)=O)[C:5]2=[N:6][CH:7]=1.[CH3:24][NH:25][CH3:26].CC([O-])(C)C.[Na+].Cl>C1(C)C=CC=CC=1.CO.O1CCOCC1>[CH3:24][N:25]([CH3:26])[C:2]1[N:3]=[C:4]2[N:10]([CH:11]([CH2:12][CH3:13])[CH2:14][CH3:15])[C:9]([OH:16])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 23676156Sodium t-butoxideHCID 57880834HCID 57880834, compound

Product 1

HCID 178446219HCID 178446219, compoundYield 32.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tert-butyl 5-bromo-2-oxo-3-(pentan-3-yl)-2,3-dihydroimidazo[4,5-b]pyrazine-1-carboxylate (200 mg, 0.52 mmol), dimethylamine (0.5 mL, 2M in THF, 1.0 mmol), Pd3(dba)2 (48 mg, 0.052 mmol), BiPhP(Cy)2 (37 mg, 0.10 mmol) and NaOtBu (150 mg, 1.56 mmol) in anhydrous toluene (4 mL) was purged with N2 for 15 second and then stirred at 120° C. for 20 minutes in microwave. The mixture was diluted with EtOAc, washed with NaHCO3 solution, dried over Na2SO4, and then concentrated in vacuo to give a dark muddy residue. The residue was dissolved in MeOH (10 mL) and treated with 1 mL 4M HCl in dioxane. After one hour, the reaction was concentrated, diluted with EtOAc, washed with NaHCO3, dried over Na2SO4, and concentrated in vacuo. Purification over silica gel (Biotage MPLC 10-70% EtOAc/hexanes) gave the title compound as a light yellow solid (42 mg, 32%).

Workup

  1. customwas purged with N2 for 15 second
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a dark muddy residue
  7. waitAfter one hour
  8. concentrationthe reaction was concentrated
  9. additiondiluted with EtOAc
  10. washwashed with NaHCO3
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated in vacuo
  13. customPurification over silica gel (Biotage MPLC 10-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-18175fb5aecf4b3491ceea10d6b2fac6
Source dataset
uspto-grants-2009_10
Patent number
US07598248B2

Reaction notes

Loading…