Sodium hydride → HCID 59367609, compound

HRID 2079793Notes

Reaction equation

HRID 2079793 reaction equation
[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:23][CH:22]3[CH:20]([CH:21]3[NH:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[CH2:19]2)=[N:16][CH:17]=1)=[O:11])[CH3:7])[CH:2]([CH3:4])[CH3:3].[H-].[Na+].Br[CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43]>CN(C=O)C>[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:19][CH:20]3[CH:22]([CH:21]3[N:24]([CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[CH2:23]2)=[N:16][CH:17]=1)=[O:11])[CH3:7])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 706082-Bromo-N,N-diethylethanamineHCID 59367561HCID 59367561, compound

Product 1

HCID 59367609HCID 59367609, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(1-Isobutoxyethoxy) 2-{6-[(naphthalen-2-ylmethyl)-amino]-3-azabicyclo[3.1.0]hex-3-yl}-pyrimidine-5-carboxamide (52 mg, 0.11 mmol) was dissolved in anhydrous DMF (2 ml) and cooled over ice. To the solution was added sodium hydride (13 mg, 0.55 mmol-60% dispersion in mineral oil) and the mixture was stirred for 15 min. To the stirring mixture was then added (2-bromoethyl)-N,N-diethylamine (22 mg, 0.12 mmol). After stirring for 30 min, the reaction was quenched by the careful addition of water and stirred for 10 min. The aqueous mixture was extracted with EtOAc (3×20 ml) and the combined organic extracts were washed with brine, dried (MgSO4) and evaporated to dryness to give the title compound as a white solid (18 mg, 29%). LCMS purity 100%, m/z 575 [M+H]+.

Workup

  1. temperaturecooled over ice
  2. stirringAfter stirring for 30 min
  3. customthe reaction was quenched by the careful addition of water
  4. stirringstirred for 10 min
  5. extractionThe aqueous mixture was extracted with EtOAc (3×20 ml)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-3427b22928fb4844a18dd04c9134aec7
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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