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

HRID 472810Notes

Reaction equation

HRID 472810 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[N:5]([N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=2)[C:6](=O)[C:7]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:6]1[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=[C:2]([CH3:1])[C:7]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178499519HCID 178499519, compound

Product 1

HCID 71742099Methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-A]pyrimidin-6-YL)acetateYield 86.9%

Procedure

To methyl 2-(5-methyl-7-oxo-2-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetate (3 g, 10.09 mmol) was added POCl3 (25 mL, 268 mmol). 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 was 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 (2.77 g, 84%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.58 (3H, s), 3.71 (3H, s), 4.04 (2H, s), 7.29 (1H, s), 7.43-7.58 (3H, m), 8.07 (2H, d, J=7.0 Hz).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling
  4. customA brown solid precipitated
  5. filtrationThe solid was 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-5662c613032d4614b46276a76832a068
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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