HCID 86598491, compound → HCID 85865908, compound

HRID 1296709Notes

Reaction equation

HRID 1296709 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([CH:17]([OH:20])[C:18]#[CH:19])=[C:15]3[N:10]([CH:11]=[N:12][CH:13]=[CH:14]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17](=[O:20])[C:18]#[CH:19])=[C:15]3[N:10]([CH:11]=[N:12][CH:13]=[CH:14]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86598491HCID 86598491, compound

Product 1

HCID 85865908HCID 85865908, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 1-[2-(3-chlorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-2-propyn-1-ol (1.41 g, 4.97 mmol) in chloroform (600 mL) was added manganese dioxide (30.3 g, 0.348 mol). The reaction mixture was stirred at 0° C. for 10 minutes then filtered through a pad of celite. The filtrate was concentrated in vacuo to provide 1-[2-(3-chlorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-2-propyn-1-one (1.40 g, 100%) as a white solid. Rf 0.37 (2:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 9.39 (s, 1H), 8.37 (d, 1H), 8.28 (d, 1H), 7.78 (s, 1H), 7.62 (d.1H), 7.52–7.40 (m, 2H), 3.17 (s, 1H); MS m/z 282 (M+1).

Workup

  1. filtrationthen filtered through a pad of celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-664fed3d988c44f5b383972f14daac09
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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