Aluminium lithium hydride → HCID 178461597, compound

HRID 522816Notes

Reaction equation

HRID 522816 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[C:7]([C:14]2[NH:15][C:16]3[C:21]([N:22]=2)=[C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][C@H:24]2[CH3:29])[N:19]=[C:18]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][C@H:31]2[CH3:36])[N:17]=3)[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:36][C@@H:31]1[CH2:32][O:33][CH2:34][CH2:35][N:30]1[C:18]1[N:17]=[C:16]2[C:21]([N:22]=[C:14]([C:7]3[CH:6]=[C:5]([CH2:3][OH:2])[CH:13]=[C:12]4[C:8]=3[CH:9]=[CH:10][NH:11]4)[NH:15]2)=[C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][C@H:24]2[CH3:29])[N:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178497308HCID 178497308, compound

Product 1

HCID 178461597HCID 178461597, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-[2,6-Bis-((R)-3-methyl-morpholin-4-yl)-9H-purin-8-yl]-1H-indole-6-carboxylic acid methyl ester (example 32, 72 mg, 146 μmol) was dissolved in 10 ml THF under argon. 1N LiAlH4 in THF (0.22 mL, 0.22 mmol) was added at 5° C., and the reaction was stirred for 2 hours at room temperature. The reaction was quenched by addition of aqueous saturated Na2SO4 (1 mL). The mixture was diluted with 30 mL of CH2Cl2 and 3 mL of isopropanol. The organic phases were separated, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (12 g SiO2, CH2Cl2/EtOH in a gradient from 100/0 to 88/12) to give the product as a solid (58 mg, 84%).

Workup

  1. customThe reaction was quenched by addition of aqueous saturated Na2SO4 (1 mL)
  2. additionThe mixture was diluted with 30 mL of CH2Cl2 and 3 mL of isopropanol
  3. customThe organic phases were separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (12 g SiO2, CH2Cl2/EtOH in a gradient from 100/0 to 88/12)

Sources & evidence

ORD record
ord-9753d97fca2444d99e67d6aff708cb93
Source dataset
uspto-grants-2016_05
Patent number
US09334271B2

Reaction notes

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