Acetonitrile → HCID 10134293, compound

HRID 1392116Notes

Reaction equation

[CH:1]1([NH:4][C:5]2(N)[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]3[C:6]2=[N:7][CH:8]=[N:9]3)[CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(N(CC)CC)C.C(#N)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]2[N:13]=[C:12]([C:14]([F:17])([F:15])[F:16])[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C:24]2[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[C:26]([O:27][CH3:28])[CH:25]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 52.5 °C

Procedure

A mixture of 6-cyclopropylamino-2-trifluoromethyladenine (46 mg, 0.2 mmol), 3,4-dimethoxyphenyl boronic acid (44 mg, 0.24 mmol), copper(II) acetate (36 mg, 0.2 mmol), triethylamine (1.0 mmol, 101 mg), anhydrous acetonitrile (4 ml) and molecular seives (˜10 pellets) was stirred at 50-55° C. for 18 hours. Ethyl acetate (20 ml) was added and the solid was removed by filtration. The filtrate was washed with 20 ml of 5% sodium bicarbonate aqueous solution. Evaporation and chromatography over SiO2 using hexane/ethylacetate/methanol (50:50:1) as elunt gave 7.9 mg of the title compound (yield 10%). 1H NMR (300 MHz, CDCl3) δ 8.10 (s, 1H), 7.39 (s, 1H), 7.13 (d, J=8.7 Hz, 2H), 6.98 (d, J=8.7 Hz, 2H), 6.35(b, 1H), 3.93 (s, 3H), 3.90 (s, 3H), 3.18 (b, 1H), 0.91 (m, 2H), 0.69 (m, 2H)

Workup

customthe solid was removed by filtration
washThe filtrate was washed with 20 ml of 5% sodium bicarbonate aqueous solution
customEvaporation and chromatography over SiO2

Sources & evidence

ORD record: ord-63b80953e212489c8ffb401f1c5763f9
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342021B2

Reaction notes

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