Ethyl 8-morpholinoimidazo[1,2-a]pyrazine-2-carboxylate → (8-Morpholinoimidazo[1,2-a]pyrazin-2-yl)methanol

HRID 1772586Notes

Reaction equation

HRID 1772586 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)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>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)[CH:10]=[CH:11][N:12]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14207617Ethyl 8-morpholinoimidazo[1,2-a]pyrazine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 117728187(8-Morpholinoimidazo[1,2-a]pyrazin-2-yl)methanolYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 1c (8.40 g, 30.4 mmol) in THF (100 mL) was added LiAlH4 (2.55 g, 60.8 mmol) in portions at 0° C. The reaction mixture was stirred at rt for 2 h. The reaction was slowly quenched with H2O (10 mL). The resulting mixture was extracted with DCM (2×100 mL), and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to obtain compound 1d as a yellow solid (3.80 g, 53% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C11H14N4O2: 235.1 (M+H). found: 235.2.

Workup

  1. customThe reaction was slowly quenched with H2O (10 mL)
  2. extractionThe resulting mixture was extracted with DCM (2×100 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b06f6b2d3ef4bb48a0705be3e4a6eaf
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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