Aluminium lithium hydride → HCID 117689132, compound

HRID 872070Notes

Reaction equation

HRID 872070 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[C:13]([O:19][CH2:20][C@H:21]2[CH2:23][C@@H:22]2[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][N:25]=2)=[N:14][C:15]([CH3:18])=[N:16][CH:17]=1)=O)C>C1COCC1>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C@H:22]2[CH2:23][C@@H:21]2[CH2:20][O:19][C:13]2[C:12]([CH2:10][OH:9])=[CH:17][N:16]=[C:15]([CH3:18])[N:14]=2)=[N:25][CH:26]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90178378HCID 90178378, compound

Product 1

HCID 117689132HCID 117689132, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1N THF solution of LAH (0.175 mL, 0.175 mmol) was added dropwise to a 0° C. solution of ethyl-4-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-2-methylpyrimidine-5-carboxylate (30 mg, 0.087 mmol) in THF (0.58 mL). The reaction mixture was slowly warmed to room temperature, and then stirred for 30 mins. The reaction mixture was re-cooled to 0° C. and the carefully quenched by dropwise addition of water (10 μL), 15% NaOH in water (20 μL), and then water (20 μL). The slurry was treated with excess Na2SO4, stirred vigorously at room temperature for 10 mins, and then filtered through a pad of Celite eluting exhaustively with 1:1 CH2Cl2/MeOH. The filtrated was concentrated in vacuo. The resulting product was sufficiently pure to use in the subsequent step without further purification. LRMS m/z (M+H) 302.4 found, 302.1 required.

Workup

  1. temperatureThe reaction mixture was re-cooled to 0° C.
  2. customthe carefully quenched by dropwise addition of water (10 μL), 15% NaOH in water (20 μL)
  3. additionThe slurry was treated with excess Na2SO4
  4. stirringstirred vigorously at room temperature for 10 mins
  5. filtrationfiltered through a pad of Celite
  6. washeluting exhaustively with 1:1 CH2Cl2/MeOH
  7. concentrationThe filtrated was concentrated in vacuo
  8. customto use in the subsequent step without further purification

Sources & evidence

ORD record
ord-ef8a78e0dc8c478a84930191a9006058
Source dataset
uspto-grants-2015_03
Patent number
US08975261B2

Reaction notes

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