Pyridine → HCID 86688017, compound

HRID 872125Notes

Reaction equation

HRID 872125 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[C:8]2[NH:9][C:10](=O)[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:7]2[N:6]=1)[CH3:2].N1C=CC=CC=1.O=P(Cl)(Cl)[Cl:37]>>[Cl:37][C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:7]2[N:6]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[C:21]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[C:8]2[N:9]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 136393900HCID 136393900, compound

Product 1

HCID 86688017HCID 86688017, compound

Procedure

2-(Ethoxymethyl)-7-(4-fluorophenyl)-3-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one (132 mg) is dissolved in POCl3 (15 mL) and pyridine (0.2 mL) and stirred overnight while heating. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with 1 M NaHCO3 aqueous solution and brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and purified by column chromatography to yield the target compound (381 mg). 1H NMR (CDCl3, 300 MHz): δ 8.11 (m, 2H), 7.73 (d, J=0.8.1 Hz, 2H), 7.26 (m, 4H), 6.87 (s, 1H), 4.70 (s, 2H), 6.66 (m, 2H), 2.41 (s, 3H), 1.26 (3H).

Workup

  1. temperaturewhile heating
  2. customthe reaction solvent is removed by distillation under reduced pressure
  3. extractionThe remainder is extracted with ethyl acetate and water
  4. washThe extracted organic layer is washed with 1 M NaHCO3 aqueous solution and brine
  5. distillationThe dehydrated organic layer is distilled under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-4a41c97e7b30432cb6a3413de771b535
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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