Acetyl chloride → 6-acetyl-9-(2-fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e] pyrimidin-5(6H)-one

HRID 1728562Notes

Reaction equation

HRID 1728562 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[NH:11][C:10](=[O:15])[N:9]3[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])[N:18]=[C:8]3[C:7]=2[CH2:6]1.[H-].[Na+].[C:32](Cl)(=[O:34])[CH3:33]>CN(C=O)C.C(OCC)(=O)C>[C:32]([N:11]1[C:12]2[CH2:13][CH2:14][N:5]([CH2:4][C:3]3[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=3[F:1])[CH2:6][C:7]=2[C:8]2=[N:18][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[CH:16][N:9]2[C:10]1=[O:15])(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 11761005HCID 11761005, compound

Product 1

HCID 190143566-acetyl-9-(2-fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e] pyrimidin-5(6H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9-(2-fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one (392 mg, 1 mmol) and 50% sodium hydride (144 mg, 3 mmol) in DMF (5 mL) was stirred at room temperature for 15 min. Acetyl chloride (1 mL) was added and stirring was continued for 30 min. The reaction was diluted with ethyl acetate and washed with water. After drying over magnesium sulfate, the solvent was removed in vacuo and the residue was subjected to flash chromatography on silica gel with 30% ethyl acetate in hexane as the eluent to afford 6-acetyl-9-(2-fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one (compound 55) and 5-acetoxy-9-(2-fluorobenzyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2c]pyrido[3,4-e]pyrimidine (compound 56) as white solids.

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. washwashed with water
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e7a06fa65a754f478485797e63cea71e
Source dataset
uspto-grants-1994_07
Patent number
US05328912

Reaction notes

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