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

HRID 399172Notes

Reaction equation

HRID 399172 reaction equation
C([N:9]1[CH2:18][CH2:17][C:16]2[NH:15][C:14](=[O:19])[N:13]3[CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[N:22]=[C:12]3[C:11]=2[CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[F:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21]1[N:22]=[C:12]2[C:11]3[CH2:10][NH:9][CH2:18][CH2:17][C:16]=3[NH:15][C:14](=[O:19])[N:13]2[CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 11760888HCID 11760888, compound

Product 1

HCID 110005642-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 9-Benzoyl-2-(2-fluorophenyl)-7,8,9,10-tetrahydroimidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one (435 mg, 1.1 mmol) in ethanol (5 mL) was added 5 mL of 50% aqueous sodium hydroxide. The mixture was refluxed for about 1 hour, and then poured into saturated aqueous ammonium chloride and extracted twice with 10% methanol/ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and triturated with methanol/ether to give 2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one, m.p. >310° C.

Workup

  1. temperatureThe mixture was refluxed for about 1 hour
  2. extractionextracted twice with 10% methanol/ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customtriturated with methanol/ether

Sources & evidence

ORD record
ord-1efcb1bd01ee42b0a1e951dd6ee0da46
Source dataset
uspto-grants-1998_10
Patent number
US05817813

Reaction notes

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