Hydrochloric Acid → HCID 68678168, compound

HRID 2233260Notes

Reaction equation

HRID 2233260 reaction equation
Cl.[CH3:2][S:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH2:17][C:18]#[N:19])=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]=[CH:6][N:5]=1.[CH2:20](N)[CH2:21][NH2:22]>C(O)C.ClCCl>[CH3:2][S:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH2:17][C:18]3[NH:22][CH2:21][CH2:20][N:19]=3)=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 68679491HCID 68679491, compound

Product 1

HCID 68678168HCID 68678168, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

Excess anhydrous hydrochloric acid in ethanol (1 ml) was added to a solution of 4-(methylthio)-6-methoxy-7-(cyanomethoxy)quinazoline (300 mg, 1.15 mmol) in dichloromethane (20 ml) and the reaction was stirred for 20 hours at 4° C. The solvent was evaporated, ethylene diamine (280 mg, 8.15 mmol) in ethanol (10 ml) was added to the residue, and the mixture was refluxed for 2 hours. Solvent evaporation in vacuo and purification by flash chromatography on silica gel, eluting with 5% methanol in dichloromethane, yielded 4-(methylthio)-6-methoxy-7-((4,5-dihydro-2-imidazolyl)methoxy)quinazoline (56 mg, 22% yield) as a white solid:

Workup

  1. customThe solvent was evaporated
  2. temperaturethe mixture was refluxed for 2 hours
  3. customSolvent evaporation
  4. customin vacuo and purification by flash chromatography on silica gel
  5. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-28d118c3a7bf4905ae6084157356fa3e
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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