HCID 22386592, compound → HCID 22386591, compound

HRID 1072426Notes

Reaction equation

HRID 1072426 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.[H][H]>[Pd].CN(C)C(=O)C>[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

5

Reactant 2

HCID 22386592HCID 22386592, compoundHCID 178418361HCID 178418361, 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 heated at 50-60° C. under 4 atmospheres of hydrogen gas in the presence of 0.36 g of 10% palladium on carbon in 80 mL of N,N-dimethylacetamide. After 4 hours the reaction mixture was filtered through silica gel in a fritted glass funnel, concentrated, dissolved in 50 mL of 2-propanol and allowed to crystallize at 4° C. The precipitate was collected by vacuum filtration, washed with 2-propanol and dried at 50° C. under vacuum to give 2.3 g (85.2% yield) of 2,4-diamino-5(4-hydroxyphenoxy)quinazoline, mp 330-341° C. (dec).

Workup

  1. filtrationAfter 4 hours the reaction mixture was filtered through silica gel in a fritted glass funnel
  2. concentrationconcentrated
  3. dissolutiondissolved in 50 mL of 2-propanol
  4. customto crystallize at 4° C
  5. filtrationThe precipitate was collected by vacuum filtration
  6. washwashed with 2-propanol
  7. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-4635e843c0bd4780a63475cffffe02da
Source dataset
uspto-grants-2005_06
Patent number
US06911446B2

Reaction notes

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