Sodium borohydride → HCID 86667376, compound

HRID 334165Notes

Reaction equation

HRID 334165 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:17](=[O:19])[CH3:18])[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:3]=1.[BH4-].[Na+]>C(O)C.C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]([OH:19])[CH3:18])[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86667375HCID 86667375, compound

Product 1

HCID 86667376HCID 86667376, compoundYield 105.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1-[2-chloro-6-morpholin-4-yl-9-(tetrahydro-pyran-2-yl)-9H-purin-8-yl]-ethanone (0.47 g, 1.29 mmol) in ethanol (8 mL) and THF (8 mL) was added sodium borohydride (49 mg, 1.30 mmol). The reaction mixture was stirred at room temperature for 1.5 h, then concentrated in vacuo. The resulting residue was dissolved in ethyl acetate and aqueous sodium bicarbonate and the phases were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic fractions were dried (Na2 SO4), filtered and concentrated in vacuo to give 1-[2-Chloro-6-morpholin-4-yl-9-(tetrahydro-pyran-2-yl)-9H-purin-8-yl]-ethanol (0.50 g, quantitative). LCMS RT=3.20 min, [M+H]+=368/370

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. customaqueous sodium bicarbonate and the phases were separated
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. customThe combined organic fractions were dried (Na2 SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-009cf56e9e814d4ab9b71d67aa610461
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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