Sodium borohydride → HCID 86667364, compound

HRID 334147Notes

Reaction equation

HRID 334147 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86667363HCID 86667363, compound

Product 1

HCID 86667364HCID 86667364, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)-2,2,2-trifluoroethanone (1.5 g, 0.0036 mol) in MeOH (22 mL) was treated with sodium tetrahydroborate (0.27 g, 0.0072 mol), 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 1-(2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)-2,2,2-trifluoroethanol (1.3 g, 86% yield). LC/MS (ESI+): m/z 423 (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-37dac30d30b14283a4f946a8e64a878e
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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