Sodium hydride → HCID 19781631, compound

HRID 257790Notes

Reaction equation

HRID 257790 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][NH:12][C:11]2=[O:20])[CH:7]=[CH:8][CH:9]=1.Cl.Cl[CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][N:12]([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[C:11]2=[O:20])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 132592941-(3-Chlorophenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

Product 1

HCID 19781631HCID 19781631, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (50% dispersion in oil) (364 mg, 7.6 mmole), previously washed in hexanes, was added to a solution of 1-(3-chlorophenyl)pyrido[2,3-d]pyrimidine-2(1H,3H)-one (500 mg, 1.9 mmole) in tetrahydrofuran (100 ml). The suspension was stirred for 5 minutes at room temperature and 4-chloromethylpyridine hydrochloride was added. The suspension was refluxed for 18 hours. The solvents were removed and H2O was added to the residue. The residue was extracted twice with ethyl acetate (2×25 ml). The organic phases were combined and the solvents removed. The residue was purified with preparative thin-layer chromatography (ethyl acetate as the eluent) yielding 116 mg (0.33 mmole, 17% yield) of 1-(3-chlorophenyl)-3-(4-pyridylmethyl)pyrido[2,3-d]pyrimidine-2(1H,3H)-one (mp 132°-134° C.), as a white solid.

Workup

  1. temperatureThe suspension was refluxed for 18 hours
  2. customThe solvents were removed
  3. additionH2O was added to the residue
  4. extractionThe residue was extracted twice with ethyl acetate (2×25 ml)
  5. customthe solvents removed
  6. customThe residue was purified with preparative thin-layer chromatography (ethyl acetate as the eluent)

Sources & evidence

ORD record
ord-3578bdcfe4e8417ba95cafa984067c57
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

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