HCID 22386581, compound → HCID 22386584, compound

HRID 2121829Notes

Reaction equation

HRID 2121829 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC=CC=3)=[CH:15][CH:14]=2)[N:5]=[CH:4][N:3]=1>CN(C)C(=O)C.[Pd]>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 22386581HCID 22386581, compound

Product 1

HCID 22386584HCID 22386584, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

4-Amino-5-(4-benzyloxyphenoxy)quinazoline (1.5 g, 4.4 mmol) was hydrogenated under 5 atm of H2 in the presence of 0.5 g of 10% Pd/C in 80 ml of N,N-dimethylacetamide at 50-60° C. After 4 hours the reaction mixture was filtered through a glass filter of silica gel, concentrated, dissolved in 80 ml of ethanol/water 4:1 (v/v) and crystallized at 4° C. The precipitate was collected by filtration, washed with ethanol and dried at 50° C. in vacuo to give 4-amino-5-(4-hydroxyphenoxy)quinazoline (0.3 g, 27.3%, m.p. 300-302° C. (dec)).

Workup

  1. filtrationAfter 4 hours the reaction mixture was filtered through a glass
  2. filtrationfilter of silica gel
  3. concentrationconcentrated
  4. dissolutiondissolved in 80 ml of ethanol/water 4:1 (v/v)
  5. customcrystallized at 4° C
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with ethanol
  8. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-d50c2c128af0431b8ad0d215e1e3e4ed
Source dataset
uspto-grants-2004_02
Patent number
US06696482B2

Reaction notes

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