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

HRID 472846Notes

Reaction equation

HRID 472846 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[N:4][N:5]2[C:10](O)=[C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:8]([CH3:17])=[N:7][C:6]=12.O=P(Cl)(Cl)[Cl:21]>>[Cl:1][C:2]1[C:3]([CH3:18])=[N:4][N:5]2[C:10]([Cl:21])=[C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:8]([CH3:17])=[N:7][C:6]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178499495HCID 178499495, compound

Product 1

HCID 86670281Methyl 2-(3,7-dichloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)acetateYield 59%

Procedure

To a solution of methyl 2-(3-chloro-7-hydroxy-2,5-di-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.160 g, 0.6 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 (0.1 g, 59%). NMR (500 MHz, DMSO-d6) δ ppm 2.44 (s, 3H), 2.57 (s, 3H), 3.68 (s, 3H), 4.00 (s, 2H). Used as is in the next step.

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-05321751d0af40e0a188fd027e5d1be3
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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