HCID 85865902, compound → HCID 86598491, compound

HRID 1296708Notes

Reaction equation

HRID 1296708 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([CH:17]=[O:18])=[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:19]([Mg]Br)#[CH:20]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([CH:17]([OH:18])[C:19]#[CH:20])=[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 2

HCID 85865902HCID 85865902, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 86598491HCID 86598491, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-chlorophenyl)pyrazolo[1,5-c]pyrimidine-3-carbaldehyde (1.5 g, 5.82 mmol) in tetrahydrofuran (50 mL) was added ethynylmagnesium bromide (17 mL, 0.5 M in tetrahydrofuran, 8.73 mmol). The reaction mixture was stirred 4 hours at room temperature then quenched with water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes:ethyl acetate) provided 1-[2-(3-chlorophenyl)pyrazolo[1.5-c]pyrimidin-3-yl]-2-propyn-1-ol (1.41 g, 85%). Rf 0.17 (2:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 9.27 (s, 1H), 7.93–7.90 (m, 2H), 7.83 (s, 1H), 7.73 (d, 1H), 7.50–7.41 (m, 2H), 5.78 (s, 1H), 2.99 (br, 1H), 2.71 (s, 1H); MS m/z 284 (M+1).

Workup

  1. customthen quenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-1bca719f6467477d98da6039f5ba9e3a
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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