Potassium Acetate → ethyl 8-methyl-2-(methylsulfanyl)-6,9-dihydro-5H-pyrrolo[3,2-h]quinazoline-7-carboxylate

HRID 626872Notes

Reaction equation

CN(/C=[C:5]1\[CH2:6][CH2:7][C:8]2[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:10]([CH3:15])[NH:11][C:12]=2[C:13]\1=O)C.[C:21]([O-])(=O)C.[K+].S(O)(O)(=O)=O.[CH3:31][NH:32][C:33](=[NH:35])[SH:34]>CN(C=O)C.C(OCC)(=O)C>[CH3:15][C:10]1[NH:11][C:12]2[C:13]3[N:35]=[C:33]([S:34][CH3:21])[N:32]=[CH:31][C:5]=3[CH2:6][CH2:7][C:8]=2[C:9]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl (6E)-6-[(dimethylamino)methylidene]-2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate 2 g (7.22 mmol) in 20 mL of anhydrous DMF, 1.41 g (14.4 mmol) of anhydrous potassium acetate and 4.0 g (14.4 mmol) of methylisothiourea sulfate were added. The reaction was stirred at 100° C. for 3 hours. The mixture was diluted with ethyl acetate, washed with H2O, dried over Na2SO4, filtered and evaporated. The crude was purified by silica gel chromagraphy (ethyl acetate: hexane 4:6) to give as major compound 0.8 g of ethyl 8-methyl-2-(methylsulfanyl)-6,9-dihydro-5H-pyrrolo[3,2-h]quinazoline-7-carboxylate (40%)

Workup

washwashed with H2O
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customThe crude was purified by silica gel chromagraphy (ethyl acetate: hexane 4:6)

Sources & evidence

ORD record: ord-c4eaa02a2c0b47cd91f253efca73c7a7
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309253B2

Reaction notes

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