Phosphorus oxychloride → HCID 86695063, compound

HRID 574327Notes

Reaction equation

HRID 574327 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:30]=[C:18]3[N:19]=[C:20]([CH3:29])[C:21]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:22](O)[N:17]3[N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:33]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:30]=[C:18]3[N:19]=[C:20]([CH3:29])[C:21]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:22]([Cl:33])[N:17]3[N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178499492HCID 178499492, compound

Product 1

HCID 86695063HCID 86695063, compoundYield 84%

Procedure

To methyl 2-(2-(3-(benzyloxy)phenyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.3 g, 0.75 mmol) was added POCl3 (3 mL). The reaction mixture was heated at reflux for 2 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 2.56 (s, 3H), 3.69 (s, 3H), 4.01 (s, 2H), 5.20 (s, 2H), 7.10 (dd, 1H), 7.29 (s, 1H), 7.32-7.37 (m, 1H), 7.39-7.45 (m, 3H), 7.51 (d, 2H), 7.63-7.69 (m, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 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-44321958687a4d6eb6471d4fe39ec9fc
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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