Dimethylformamide → HCID 86754384, compound

HRID 1584750Notes

Reaction equation

HRID 1584750 reaction equation
O[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[H-].[Na+].Cl[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1.CN(C=[O:26])C>>[N:17]1[CH:18]=[CH:19][CH:20]=[N:21][C:16]=1[O:26][CH:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=2)[C:8]1=[O:12]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 86754384HCID 86754384, compound

Conditions

Temperature
100 °C

Procedure

6-Hydroxytetralone (31 mmol) was dissolved in dry DMF (50 mL), chilled in an ice/water bath and blanketed with a stream of nitrogen. NaH (60% in mineral oil, 31 mmol) was added slowly and in portions. Once gas evolution ceased, 2-chloropyrimidine (31 mmol) was added, the ice bath was removed and the solution heated at 100° C. for 1.5 hours. It was then cooled to room temperature and the solvent was removed in vacuo. The residue was treated with water and CH2Cl2 (200 mL each). Evaporation of the organic layer yielded crude material which was purified by flash chromatography (1:1 hexane:EtOAc) to afford 6-[(2-pyrimidinyl)oxyl-tetralone as a light yellow powder.

Workup

  1. temperaturechilled in an ice/water bath
  2. customthe ice bath was removed
  3. temperatureIt was then cooled to room temperature
  4. customthe solvent was removed in vacuo
  5. additionThe residue was treated with water and CH2Cl2 (200 mL each)
  6. customEvaporation of the organic layer
  7. customyielded crude material which
  8. customwas purified by flash chromatography (1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-d5df54f475e04f6ba52998e4781f0ed7
Source dataset
uspto-grants-1999_08
Patent number
US05935958

Reaction notes

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