Phosphorus oxychloride → HCID 86711218, compound

HRID 1475943Notes

Reaction equation

O[C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:3]=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178469340HCID 178469340, compound

Product 1

HCID 86711218HCID 86711218, compoundYield 60.4%

Conditions

Temperature: 115 °C

Procedure

Ethyl 7-hydroxy-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylate (1.26 g; 4.03 mmol) was suspended in phosphoryl chloride (8 mL; 88 mmol) and the mixture was heated to 115° C. for 1 h. The reaction mixture was allowed to cool to room temperature and then carefully quenched into a cold mixture of methylene chloride and saturated sodium bicarbonate. The basic aqueous layer was back extracted once with methylene chloride and the combined organic phases were washed with brine. Concentration afforded a crude solid which was triturated in methanol (15 mL) at 60° C. for 5 min. and then at room temperature for an hour. Filtration afforded 808 mg (60%) of the title compound. LCMS m/z 332.1 (M+H)+, ret. time=2.77 min.

Workup

temperatureto cool to room temperature
customcarefully quenched into a cold mixture of methylene chloride and saturated sodium bicarbonate
extractionThe basic aqueous layer was back extracted once with methylene chloride
washthe combined organic phases were washed with brine
concentrationConcentration
customafforded a crude solid which
customwas triturated in methanol (15 mL) at 60° C. for 5 min.
waitat room temperature for an hour
filtrationFiltration

Sources & evidence

ORD record: ord-5c425133b0b440a989a16e319369cbd3
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018395B2

Reaction notes

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