HCID 178418336, compound → HCID 178418817, compound

HRID 1864588Notes

Reaction equation

HRID 1864588 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][C:13]2[NH:14][N:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:21]([Mg]Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.Cl[Ni]Cl>[CH2:21]([C:2]1[N:11]=[C:10]([NH:12][C:13]2[NH:14][N:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 178418336HCID 178418336, compoundHCID 178418784HCID 178418784, compound

Product 1

HCID 178418817HCID 178418817, compound

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of the above-prepared (2-chloroquinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (123 mg, 0.43 mmol) in THF (5 mL) is added NiCl2 (dppp) (12 mg, 2.1.10−5 mol), followed by 1M benzylmagnesium chloride in THF (2.15 mL, 2.15 mmol). The solution is heated at 50° C. for 20 hours and the reaction mixture is then quenched with aqueous NH4Cl and the product extracted in ethyl acetate. The solvent is evaporated and the residue purified by flash chromatography to yield the desired (2-benzyl-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine.

Workup

  1. customthe reaction mixture is then quenched with aqueous NH4Cl
  2. extractionthe product extracted in ethyl acetate
  3. customThe solvent is evaporated
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-62ceae7c3031427892e7458bde8d4675
Source dataset
uspto-grants-2009_12
Patent number
US07625913B2

Reaction notes

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