Sodium triacetoxyborohydride → 2-(1-((2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol

HRID 1692874

Reaction equation

HRID 1692874 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]=O)[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.[NH:25]1[CH2:30][CH2:29][CH:28]([C:31]([OH:34])([CH3:33])[CH3:32])[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:17][N:25]3[CH2:30][CH2:29][CH:28]([C:31]([OH:34])([CH3:33])[CH3:32])[CH2:27][CH2:26]3)[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

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 52003212-(4-Piperidyl)-2-propanolHCID 596034642-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine-8-carbaldehyde

Product 1

HCID 596035392-(1-((2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-olYield 98.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-8-carbaldehyde (245 mg, 0.696 mmol), 2-(4-piperidyl)-2-propanol (110 mg, 0.77 mmol) and sodium triacetoxyborohydride (162 mg, 0.77 mmol) in 1,2-dichloroethane (10 mL) was stirred at room temperature for 30 minutes. The reaction mixture was then diluted with saturated aqueous sodium bicarbonate. The aqueous layer was then extracted with DCM. The combined organic extracts were then washed with water, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (0-100% gradient EtOAc-heptane) to give the title compound (328 mg, 98%). LCMS: M+H+=480.2.

Workup

  1. extractionThe aqueous layer was then extracted with DCM
  2. washThe combined organic extracts were then washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0-100% gradient EtOAc-heptane)

Sources & evidence

ORD record
ord-2e57d51323a34bf2ab721a3ded651eae
Source dataset
uspto-grants-2012_04
Patent number
US08158625B2

Linked notes

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