HCID 58842531, compound → HCID 58842306, compound

HRID 1270440Notes

Reaction equation

HRID 1270440 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>CO.[Pd]>[C:20]1([C:14]2([CH2:13][NH:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[CH:2][N:11]=3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 58842531HCID 58842531, compound

Product 1

HCID 58842306HCID 58842306, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2-chloro-quinazolin-4-yl)-(1-phenyl-cyclohexylmethyl)-amine (0.065 g; 0.18 mmol) in anhydrous methanol (2 mL) was treated with 10% palladium on carbon (200 mg) and placed under an atmosphere of hydrogen (45 psi). The reaction mixture was shaken at room temperature for 3 h. The reaction mixture was filtered through celite and evaporated. The crude residue was purified by column chromatography on silicia gel using 9:1 ethyl acetate:hexane as the eluent to give 0.052 g (1-phenyl-cyclohexylmethyl)-quinazolin-4-yl-amine as a white foam. LCMS m/z=318.2 (M+H)+

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated
  3. customThe crude residue was purified by column chromatography on silicia gel

Sources & evidence

ORD record
ord-dfb5097f92d04ee6b97f746288bd2db0
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

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