Sodium hydride → HCID 58054334, compound

HRID 2066411Notes

Reaction equation

HRID 2066411 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[C:18]1[N:19]([CH3:34])[C:20]2[C:25]([N:26]=1)=[C:24]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:23]=[C:22]([Cl:33])[N:21]=2>CN(C=O)C.CCOC(C)=O>[Cl:33][C:22]1[N:21]=[C:20]2[C:25]([N:26]=[C:18]([O:16][CH:13]3[CH2:14][CH2:15][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:11][CH2:12]3)[N:19]2[CH3:34])=[C:24]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:23]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 58054330HCID 58054330, compound

Product 1

HCID 58054334HCID 58054334, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (0.327 g, 8.18 mmol) in DMF (31 mL) at 0° C. was added 1-tert-Butoxycarbonyl-4-hydroxypiperidine (1.266 g, 6.29 mmol). After 10 min, 4-(8-bromo-2-chloro-9-methyl-9H-purin-6-yl)morpholine (2.09 g, 6.29 mmol) was added. The mixture was stirred at rt for 3 h. Diluted with EtOAc, the mixture was washed with ½ brine (2×), brine, and dried (Na2SO4). The crude (3.075 g) was used directly for further transformations. LCMS: M+H+=453.4.

Workup

  1. washthe mixture was washed with ½ brine (2×), brine
  2. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-815df42102f740d0b5cbae4a62c2c189
Source dataset
uspto-grants-2012_10
Patent number
US08293736B2

Reaction notes

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