Dimethylformamide → HCID 68388893, compound

HRID 927291Notes

Reaction equation

C[Si](C)(C)[O:3][C:4]1[N:13]=[C:12]([O:14][Si](C)(C)C)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.Br[CH2:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26]([O:28][CH3:29])=[O:27].CN(C=O)C.O1CCOCC1>CO>[CH3:29][O:28][C:26]([C:25]1[CH:24]=[C:23]([CH:32]=[CH:31][CH:30]=1)[CH2:22][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12](=[O:14])[NH:13][C:4]1=[O:3])=[O:27]

Participants

Conditions

Temperature: 122.5 °C

Procedure

The intermediate product 2,4-di(trimethylsilyloxy)quinazoline, methyl 3-(bromomethyl)benzoate (2.1 g, 9.2 mmol) and DMF (1 mL) were added in turn into a 50 mL single-mouth flask, and then the temperature were raised to 115-130° C. and reacted for 3 hours. 1,4-dioxane (6 mL) and methanol (10 mL) were added after the reaction mixture was cooled to 100° C. Then the mixture was refluxed for 30 minutes. The mixture was filtered after it was cooled to room temperature. The precipitate was washed with water (20 mL) and methonal (10 mL), respectively, and dried to give the title compound (1.6 g, 83.7% yield) as white powder. 1H NMR (DMSO-d6): 11.76 (s, 1H), 8.00 (dd, J=7.8 and 1.2 Hz, 1H), 7.89 (s, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.65-7.43 (m, 3H), 7.25-7.20 (m, 2H), 5.36 (s, 2H), 3.80 (s, 3H). MS: m/z 311.1 [M+H]+.

Workup

customreacted for 3 hours
temperaturewas cooled to 100° C
temperatureThen the mixture was refluxed for 30 minutes
filtrationThe mixture was filtered after it
temperaturewas cooled to room temperature
washThe precipitate was washed with water (20 mL) and methonal (10 mL)
customrespectively, and dried

Sources & evidence

ORD record: ord-b4d0ff70e3974d40a92291668c665df4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290460B2

Reaction notes

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