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 2371678Notes

Reaction equation

HRID 2371678 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-126e4e4efc3f49f09dfa501d19233a76
Source dataset
uspto-grants-1992_03
Patent number
US05095015

Reaction notes

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