Cesium fluoride → 1,3-Dimethyl-5-(2-propen-1-yl)-2,4(1H,3H)-quinazolinedione

HRID 552374Notes

Reaction equation

I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:15])[N:5]([CH3:14])[C:6](=[O:13])[N:7]2[CH3:12].[F-].[Cs+].[CH2:18](B1OC(C)(C)C(C)(C)O1)[CH:19]=[CH2:20]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:20]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:15])[N:5]([CH3:14])[C:6](=[O:13])[N:7]2[CH3:12])[CH:19]=[CH2:18]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of Step 4 intermediate (40 g, 126 mmol) in 1,4-dioxane (1.3 lit) was added cesium fluoride (38.3 g, 252 mmol) and allylboronic acid pinacol ester (42.5 ml, 225 mmol) under nitrogen atmosphere and the mixture was degassed for 10 min. Tetrakis(triphenylphosphine)palladium(0) (14.46 g, 12 mmol) catalyst was added and the mixture was stirred at 100° C. for 20 h under nitrogen atmosphere. The mixture was diluted with water (500 ml) and extracted with ethyl acetate (3×500 ml). The combined extracts were concentrated and the residue obtained was purified by silica gel column chromatography to give 26.5 g of the product as an off-white solid; 1H NMR (δ ppm, CDCl3, 300 MHz): 7.54 (t, J=7.8, 1H); 7.08 (t, J=6.9, 2H); 6.18-6.00 (m, 1H); 5.06-4.95 (m, 2H); 4.04 (d, J=6.3, 2H); 3.60 (s, 3H); 3.45 (s, 3H). MS (m/z): 231.37 ([M+H]+).

Workup

customthe mixture was degassed for 10 min
extractionextracted with ethyl acetate (3×500 ml)
concentrationThe combined extracts were concentrated
customthe residue obtained
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-912f7206d86f4304947d6b6d75e0f511
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951814B2

Reaction notes

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