2-Methyl-1-butene → 3-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanoic acid

HRID 856008

Reaction equation

HRID 856008 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH:24]=[O:25])=[CH:18][CH:17]=4)[CH:13]=[N:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(CC)=C.[OH:31]P([O-])(O)=O.[Na+].Cl([O-])=O.[Na+]>CC(O)(C)C.C1COCC1>[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]([OH:31])=[O:25])=[CH:20][CH:21]=4)[CH:13]=[N:12][C:11]=23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 112402-Methyl-1-buteneHCID 23668197Sodium Chlorite2×HCID 23672064Monosodium phosphate2×HCID 586916073-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanal

Product 1

HCID 586915983-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanoic acid

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanal (2-5, 278 mg, 0.850 mmol, 1 equiv) in a 4:1 mixture of THF and t-BuOH (20 mL) was treated with 2-methyl butene (5 mL), an aqueous solution of sodium phosphate monobasic (0.14 M, 234 mg, 1.70 mmol, 2 equiv) and sodium chlorite (197 mg, 2.18 mmol, 2.57 equiv). After 1 hour at room temperature, additional solid sodium phosphate monobasic (278 mg, 1.70 mmol, 2 equiv) and sodium chlorite (197 mg, 2.18 mmol, 2.57 equiv) were added. The reaction mixture was stirred for an additional 4 hours, concentrated and the residue dissolved in EtOAc (100 mL) then washed with a 25:1 mixture of aqueous 10% sodium bisulfite solution and 10% potassium hydrogen sulfate solution (2×100 mL). The organic layer was dried over sodium sulfate and concentrated to afford 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanoic acid (4-1) as a yellow solid. LRMS m/z: Calc'd for C21H18N3O2 (M+H) 344.4, found 344.1.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue dissolved in EtOAc (100 mL)
  3. washthen washed with a 25:1 mixture of aqueous 10% sodium bisulfite solution and 10% potassium hydrogen sulfate solution (2×100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-91e8108a05f4400cbcc76edb61814918
Source dataset
uspto-grants-2007_08
Patent number
US07262199B2

Linked notes

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