Ammonia → 5-AMINO-4-HYDROXYQUINAZOLINE

HRID 2112075Notes

Reaction equation

HRID 2112075 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:3]=1[C:4]([NH2:6])=[O:5].[CH3:12]OC(OC)OC.S(=O)(=O)(O)O.N>CN(C)C(=O)C.CO>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:5])[NH:6][CH:12]=[N:11]2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 21272453HCID 21272453, compound

Product 1

HCID 1354391415-AMINO-4-HYDROXYQUINAZOLINE

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

900 mg (5.958 mmol) 2,6-diaminobenzamide are dissolved in 3.6 ml N,N-dimethylacetamide and combined with 6.3 ml (57.01 mmol) trimethylorthoformate and 792 μl (8.865 mmol) 98% sulphuric acid. After 16 h at 25° C. the reaction mixture is taken up with 20 ml of methanol and the solvent is eliminated in vacuo. The residue is again taken up in 20 ml of methanol, neutralised with concentrated ammonia. The solvent is eliminated in vacuo and the residue purified by chromatography. The carrier used is silica gel and the eluant used is dichloromethane, to which 7% of a mixture of 90% methanol and 10% saturated aqueous ammonia solution are added.

Workup

  1. customthe residue purified by chromatography
  2. additionto which 7% of a mixture of 90% methanol and 10% saturated aqueous ammonia solution are added

Sources & evidence

ORD record
ord-96aaa5a6cebb4c6a95e2a5aa678e4360
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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