Water → (8-Morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol

HRID 718568Notes

Reaction equation

HRID 718568 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([C:16](OCC)=[O:17])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH4+].[Cl-].O>C1COCC1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 117728723Ethyl 8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

Product 1

HCID 117728752(8-Morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of compound 5c (14 g, 51 mmol) in THF (400 mL) was cooled in an ice-water bath under an argon atmosphere and treated with lithium aluminium hydride (1M in THF, 51 mL, 51 mmol) dropwise. After 1 h, saturated NH4Cl solution (20 mL) was added slowly to quench the reaction, followed by 200 mL of water. The reaction mixture was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give compound 5d as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.98 (d, J=5.6 Hz, 1H), 7.77 (s, 1H), 6.05 (d, J=5.9 Hz, 1H), 4.81 (s, 2H), 3.91 (s, 8H), 2.71 (br. s., 1H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with EtOAc (2×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ed87fe51c7c04195b18584756b416f5c
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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