Phosphorus oxychloride → HCID 86692835, compound

HRID 928246Notes

Reaction equation

HRID 928246 reaction equation
[C:1]1([C:11]2[CH:20]=[C:14]3[NH:15][CH:16]=[CH:17][C:18](=O)[N:13]3[N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:18]1[N:13]2[N:12]=[C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH:20]=[C:14]2[N:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516530HCID 178516530, compound

Product 1

HCID 86692835HCID 86692835, compoundYield 100%

Procedure

2-(naphthalen-1-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one (4.0 g, 15 mmol) is heated in phosphoryl chloride (28 mL) in a sealed vial at 105° C. and stirred for 5 hours. The crude reaction mixture is cooled to room temperature and poured slowly over ice. The resulting solid is collected on a Buchner funnel to provide 7-chloro-2-(1-naphthyl)pyrazolo[1,5-a]pyrimidine (4.3 g, yield 100%). LCMS: (AA) M+1 280.

Workup

  1. customThe crude reaction mixture
  2. additionpoured slowly over ice
  3. customThe resulting solid is collected on a Buchner funnel

Sources & evidence

ORD record
ord-d8eede88fea94765ab8fcf9ed30c2ea0
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

Loading…