HCID 22386592, compound → HCID 22386591, compound

HRID 1067493Notes

Reaction equation

HRID 1067493 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]CC3C=CC=CC=3)=[CH:16][CH:15]=2)[N:3]=1>CN(C)C(=O)C.[Pd]>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[N:3]=1

Participants

4

Reactant 1

HCID 22386592HCID 22386592, compound

Product 1

HCID 22386591HCID 22386591, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

2,4-Diamino-5-(4-benzyloxyphenoxy)quinazoline (3.6 g, 10 mmol) was hydrogenated under 4 atm of H2 in the presence of 0.36 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 50 ml of 2-propanol and crystallized at 4° C. The precipitate was collected by filtration, washed with 2-propanol and dried at 50° C. in vacuo to give 2,4-diamino-5-(4-hydroxyphenoxy)quinazoline (2.3 g, 85.2%, m.p. 330-341° 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 50 ml of 2-propanol
  5. customcrystallized at 4° C
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with 2-propanol
  8. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-29ab58c828a74329bf2cfaeba2bc03da
Source dataset
uspto-grants-2001_06
Patent number
US06248771B1

Reaction notes

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