Tetrahydrofuran → Diethylether ethylacetate

HRID 257789Notes

Reaction equation

HRID 257789 reaction equation
ClC1C=C(C=CC=1)NC1C(CN)=CC=CN=1.C(N1C=CN=C1)(N1C=CN=C1)=[O:18].ClC1C=C(N2C3N=CC=CC=3CNC2=O)C=CC=1.[O:47]1[CH2:51][CH2:50][CH2:49][CH2:48]1>>[C:48]([O:47][CH2:51][CH3:50])(=[O:18])[CH3:49].[CH2:48]([O:47][CH2:51][CH3:50])[CH3:49]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 132592941-(3-Chlorophenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-oneHCID 19781588HCID 19781588, compound

Product 1

HCID 21584169Diethylether ethylacetateYield 50%

Procedure

Sodium hydride (previously washed in hexanes) was added to a solution of 2-(3-chloroanilino)-3-aminomethylpyridine (10.3 g, 44.1 mmole) in tetrahydrofuran (200 ml). The solution was stirred at room temperature for 5 minutes. 1,1'-Carbonyldiimidazole (10.7 g, 66.1 mmole) was added gradually to the solution with stirring; after the addition the solution was refluxed for 22 hours. The solvents were removed and H2O was added to the residue. The solid material was extracted in ethyl acetate, washed with H2O and dried over MgSO4. The MgSO4 was removed by filtration and the solvents by evaporation. The product was recrystallized out of ethyl acetate/ethyl ether yielding 5.7 g (21.9 mmole, 50% yield) of 1-(3-chlorophenyl)pyrido[2,3-d]pyrimidine-2(1H,3H)-one (mp 188°-187° C.), as a tan solid.

Workup

  1. washSodium hydride (previously washed in hexanes)
  2. stirringwith stirring
  3. additionafter the addition the solution
  4. temperaturewas refluxed for 22 hours
  5. customThe solvents were removed
  6. additionH2O was added to the residue
  7. extractionThe solid material was extracted in ethyl acetate
  8. washwashed with H2O
  9. dry with materialdried over MgSO4
  10. customThe MgSO4 was removed by filtration
  11. customthe solvents by evaporation

Sources & evidence

ORD record
ord-e0755c513d5243bbab8eaa043e0680ed
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

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