Sodium hydride → HCID 14653247, compound

HRID 1199479Notes

Reaction equation

HRID 1199479 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]1[NH:13][C:14](=[O:26])[C:15]([C:24]#[N:25])=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1.[H-].[Na+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>C1COCC1>[C:24]([C:15]1[C:14](=[O:26])[N:13]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:12]([C:7]2[C:8]3[C:3](=[C:2]([Br:1])[CH:11]=[CH:10][CH:9]=3)[CH:4]=[CH:5][CH:6]=2)=[N:17][C:16]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)#[N:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate2×HCID 135847668HCID 135847668, compound

Product 1

HCID 14653247HCID 14653247, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,6-Dihydro-2-(5-bromo-1-naphthalenyl)-6-oxo-4-phenyl-5-pyrimidinecarbonitrile (4.0 g, 9.9 mmol) was added portionwise to a suspension of sodium hydride (60% dispersion in mineral oil, washed with hexane, 0.6 g, 14.9 mmol) in dry THF (80 mL). After 5 minutes the mixture became a homogeneous solution. Neat t-butyl bromoacetate (2.9 g, 14.9 mmol) was added in one portion and the mixture was refluxed for 18 hours. Additional t-butyl bromoacetate (0.4 g, 2.0 mmol) was added and reflux was continued for 2 hours. The reaction mixture was cooled to room temperature and quenched with water. The mixture was partitioned between water (50 mL) and CHCl3 (100 mL), and the aqueous layer was extracted with CHCl3 (2×50 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated in vacuo to give an orange foam (5.4 g). The material was purified by radial preparative thin-layer (Chromatotron) chromatography with elution by EtOAc/hexanes (20:80) to give the pure product (3.0 g, 59%).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. temperaturereflux
  3. waitwas continued for 2 hours
  4. customquenched with water
  5. customThe mixture was partitioned between water (50 mL) and CHCl3 (100 mL)
  6. extractionthe aqueous layer was extracted with CHCl3 (2×50 mL)
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56827a0b34e241b282d1b1fe9144d5fc
Source dataset
uspto-grants-1990_02
Patent number
US04900829

Reaction notes

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