Phosphorus oxychloride → Methyl 2-(7-chloro-5-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 472825Notes

Reaction equation

HRID 472825 reaction equation
O[CH:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[NH:5][C:4]([CH3:17])=[C:3]1[CH2:18][C:19]([O:21][CH3:22])=[O:20].O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[N:5]=[C:4]([CH3:17])[C:3]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136350318Methyl2-(7-hydroxy-5-methyl-3-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetate

Product 1

HCID 86670268Methyl 2-(7-chloro-5-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetateYield 90%

Procedure

To methyl 2-(7-hydroxy-5-methyl-3-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.5 g, 1.68 mmol) was added POCl3 (1 mL). The reaction mixture was heated at reflux for 1 h. After cooling, the reaction mixture was added drop-wise to ice-water. A brown solid precipitated. The solid were filtered and washed with water, then dissolved in ethyl acetate. The organic solution was washed with saturated NaHCO3 and dried over sodium sulfate. The solvent was evaporated to give the title compound (0.48 g, 90%). 1H-NMR (500 MHz, MeOD) δ ppm 2.66 (3H, s), 3.77 (3H, s), 4.04 (2H, s), 7.26 (1H, s), 7.42 (2H, s), 8.09 (2H, s), 8.57 (1H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling
  4. customA brown solid precipitated
  5. filtrationThe solid were filtered
  6. washwashed with water
  7. dissolutiondissolved in ethyl acetate
  8. washThe organic solution was washed with saturated NaHCO3
  9. dry with materialdried over sodium sulfate
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-511faa31591e4bb7b8a30e30928ab0f8
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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