Dimethylacetamide → HCID 135556679, compound

HRID 1532630Notes

Reaction equation

HRID 1532630 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2OC2C=CC(OCC3C=CC=CC=3)=CC=2)[N:5]=[CH:4][N:3]=1.[H][H].CN(C)[C:31](=[O:33])[CH3:32]>[Pd]>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:6]2[CH:7]=[CH:8][C:31]([OH:33])=[CH:32][CH:11]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 22386581HCID 22386581, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135556679HCID 135556679, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-Amino-5-(4-benzyloxyphenoxy)quinazoline (1.5 g, 4.4 mmol) was heated at 50-60° C. under 5 atmospheres of hydrogen gas in the presence of 0.5 g of 10% palladium on carbon in 80 mL of N,N-dimethylacetamide. After 4 hours the reaction mixture was filtered through a fritted glass funnel containing silica gel, concentrated, dissolved in 80 mL of ethanol/water 4/1 (v/v) and allowed to crystallize at 4° C. The precipitate was collected by vacuum filtration, washed with ethanol and dried at 150° C. under vacuum to give 0.3 g (27.3% yield) of 4-amino-5-(4-hydroxyphenyl)quinazoline, m.p. 300-302° C. (dec).

Workup

  1. filtrationAfter 4 hours the reaction mixture was filtered through a fritted glass funnel
  2. additioncontaining silica gel
  3. concentrationconcentrated
  4. dissolutiondissolved in 80 mL of ethanol/water 4/1 (v/v)
  5. customto crystallize at 4° C
  6. filtrationThe precipitate was collected by vacuum filtration
  7. washwashed with ethanol
  8. customdried at 150° C. under vacuum

Sources & evidence

ORD record
ord-02dc6c26ae9949e6a51256b2658d476f
Source dataset
uspto-grants-2001_03
Patent number
US06204267B1

Reaction notes

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