Sodium borohydride → HCID 86667346, compound

HRID 334127

Reaction equation

HRID 334127 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]=[O:18])[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:17][OH:18])[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 596034642-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine-8-carbaldehyde

Product 1

HCID 86667346HCID 86667346, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-8-carbaldehyde (3.8 g, 11 mmol) in MeOH (22 mL) was treated with sodium tetrahydroborate (0.817 g, 22 mmol), and stirred at room temperature for 1 hour. The reaction was quenched with water and extracted with EtOAc. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated. The crude material was purified with isco with 0-80% EtOAc/hexane to give the pure (2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)methanol (3.4 g, 89% yield). LC/MS (ESI+): m/z 354 (M+H)

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified with isco with 0-80% EtOAc/hexane

Sources & evidence

ORD record
ord-d773c2996a754e139ddc817a860e030d
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Linked notes

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