Water → HCID 59408906, compound

HRID 1422493Notes

Reaction equation

HRID 1422493 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][NH:18][C:19]2[N:27]=[C:26]([C:28]3[CH:29]=[N:30][CH:31]=[C:32]([F:34])[CH:33]=3)[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[CH:35]([CH3:40])[C:36](OC)=[O:37])=[CH:8]1.O>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][NH:18][C:19]2[N:27]=[C:26]([C:28]3[CH:29]=[N:30][CH:31]=[C:32]([F:34])[CH:33]=3)[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[CH:35]([CH3:40])[CH2:36][OH:37])=[CH:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67377267HCID 67377267, compound

Product 1

HCID 59408906HCID 59408906, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (230 mg, 6.1 mmol) was added in portions to a 0° C. solution of methyl 2-(6-(2-(1H-indol-3-yl)ethylamino)-2-(5-fluoropyridin-3-yl)-9H-purin-9-yl)propanoate (282 mg, 0.61 mmol) in anhydrous THF (15 mL). The stirred reaction mixture was allowed to warm to rt over 2 h, then water was added carefully. The mixture was extracted with EtOAc (50 ml×3). The organic fractions were combined, washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (0 to 5% solvent B in dichloromethane; solvent B=2M ammonia in methanol) to afford the partially purified title product. This was further purified by preparative TLC (5% solvent B in dichloromethane) to provide the title compound as a white solid.

Workup

  1. customThe stirred reaction mixture
  2. extractionThe mixture was extracted with EtOAc (50 ml×3)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (0 to 5% solvent B in dichloromethane; solvent B=2M ammonia in methanol)
  7. customto afford the
  8. custompartially purified title product
  9. customThis was further purified by preparative TLC (5% solvent B in dichloromethane)

Sources & evidence

ORD record
ord-4185f708355c4ae39b2f467594962fd1
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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