Aluminium lithium hydride → HCID 57886011, compound

HRID 659332Notes

Reaction equation

HRID 659332 reaction equation
[CH2:1]([N:8]1[C:13](=O)[CH2:12][NH:11][C:10]2[N:15]=[CH:16][C:17](I)=[CH:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:15]=[CH:16][CH:17]=[CH:18][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 578859791-Benzyl-7-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 57886011HCID 57886011, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (50 mg) was dissolved in anhydrous tetrahydrofuran and added to LiAlH4 (1 M in tetrahydrofuran, 9.0 eq) over 2 minutes. After stirring for 35 minutes at room temperature, the reaction mixture was quenched with wet ether, diluted with ethyl acetate and H2O, and filtered. The organic phase was isolated, dried, filtered, and concentrated. Silica gel chromatography (0-10% methanol in CH2Cl2) gave the title compound as a pale yellow film (10% yield). M.p. (film), LCMS: m/z=226.19 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.35-3.40 (m, 2H), 3.52-3.57 (m, 2H), 4.40 (s, 2H), 4.83 (bs, 1H), 6.41-6.50 (m, 1H), 6.56-6.63 (m, 1H), 7.20-7.38 (m, 5H), 7.43 (d, J=1.2H).

Workup

  1. customthe reaction mixture was quenched with wet ether
  2. additiondiluted with ethyl acetate and H2O
  3. filtrationfiltered
  4. customThe organic phase was isolated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9399847c914e4f61a9bb95dc8459cd12
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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