Diethyl Ether → Diethyl [5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methylphosphonate

HRID 394113Notes

Reaction equation

Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][NH:8][C:9](=[O:21])[N:10]2[C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])=[C:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[CH:4]=1.[CH2:29]([O:31][P:32]([O:36]CC)[O:33][CH2:34][CH3:35])[CH3:30].CCOCC.CCCCCC>CN(C=O)C>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:5]1[CH:4]=[C:3]([CH2:2][P:32](=[O:36])([O:33][CH2:34][CH3:35])[O:31][CH2:29][CH3:30])[CH:12]=[C:11]2[C:6]=1[CH2:7][NH:8][C:9](=[O:21])[N:10]2[C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-(bromomethyl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydroquinazolin-2(1H)-one (55 mg, 0.11 mmol) and triethylphosphite (0.8 mL, 4.66 mmol) in DMF (0.5 mL) was stirred at 100° C. for 1.75 h. After it was cooled to rt, the resulting mixture was treated with ether and hexane to form a precipitate. Filtration of the precipitate provided diethyl [5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methylphosphonate as a white solid. 1H NMR (CDCl3, 500 MHz): δ 1.20 (m, 6H), 3.01 (s, 1H), 3.06 (s, 1H), 3.97 (m, 4H), 4.34 (abq, 2H, J=14.1 Hz), 5.12 (s, 1H), 6.12 (s, 1H), 6.86 (s, 1H), 7.26-7.60 (m, 7H). MS (API-ES+): 553 (M+H).

Workup

temperatureAfter it was cooled to rt
customto form a precipitate
filtrationFiltration of the precipitate

Sources & evidence

ORD record: ord-ecba6a2147f44adaaab952e861c345b4
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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