Dichloromethane → HCID 178433171, compound

HRID 505329Notes

Reaction equation

I.[Br:2][C:3]1[CH:4]=[C:5]([Cl:16])[CH:6]=[C:7]2[C:12]=1[N:11]=[C:10](SC)[NH:9][CH:8]2[CH3:15].[O:17]([CH2:24][CH2:25][NH2:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].C(Cl)Cl>C(#N)C.OO>[Br:2][C:3]1[CH:4]=[C:5]([Cl:16])[CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([NH:26][CH2:25][CH2:24][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:9][CH:8]2[CH3:15]

Participants

Conditions

Temperature: 200 °C

Procedure

8-Bromo-6-chloro-4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (141 mg, 0.33 mmol) and 2-phenoxyethyl amine (53.5 mg, 0.39 mmol) were dissolved in acetonitrile (1 ml) and heated to 200° C. in a sealed tube in a microwave oven for 30 minutes. After cooling the reaction was treated with 1N aqueous sodium hydroxide solution, methylene chloride and 5 to 7 drops of 30% aqueous hydrogen peroxide solution. After the reaction has ceased the layers were separated and the aqueous phase was extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, the solvent was evaporated and the residue was purified by column chromatography (CH2Cl2:MeOH:aq conc NH3=9:1:0.1) to yield the title compound as an off-white solid (60 mg, 47%).

Workup

temperatureAfter cooling the reaction
customwere separated
extractionthe aqueous phase was extracted with methylene chloride
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
customthe solvent was evaporated
customthe residue was purified by column chromatography (CH2Cl2:MeOH:aq conc NH3=9:1:0.1)

Sources & evidence

ORD record: ord-c91c674f21094a928dd3ad36b2a9e099
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781441B2

Reaction notes

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