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

HRID 574339Notes

Reaction equation

HRID 574339 reaction equation
[Br:1][C:2]1[CH:17]=[C:5]2[NH:6][C:7]([CH3:16])=[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:9](=O)[N:4]2[N:3]=1.O=P(Cl)(Cl)[Cl:20]>>[Br:1][C:2]1[CH:17]=[C:5]2[N:6]=[C:7]([CH3:16])[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:20])[N:4]2[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178499518HCID 178499518, compound

Product 1

HCID 86670270Methyl 2-(2-bromo-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetateYield 83%

Procedure

To methyl 2-(2-bromo-5-methyl-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetate (180 mg, 0.600 mmol) was added POCl3 (1 mL, 10.73 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 to give the title compound (158 mg, 83%). 1H NMR (500 MHz, DMSO-d6) δ 2.56 (3H, s), 3.69 (3H, s), 4.01 (2H, s), 6.99 (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 was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-19be1be318e2441b93c4faa108a68736
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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