Methanol → 1-(4-Bromophenyl)-9-methyl-2-(2,3,4-trifluorophenoxy)-1,9-dihydro-6H-purin-6-one

HRID 1674711Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[N:14]=[CH:13][N:12]([CH3:18])[C:11]=3[N:10]=[C:9]2Cl)=[CH:4][CH:3]=1.[F:20][C:21]1[C:26]([F:27])=[C:25]([F:28])[CH:24]=[CH:23][C:22]=1[OH:29].CO>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[N:14]=[CH:13][N:12]([CH3:18])[C:11]=3[N:10]=[C:9]2[O:29][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[C:26]([F:27])[C:21]=2[F:20])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

1-(4-Bromophenyl)-2-chloro-9-methyl-1,9-dihydro-6H-purin-6-one (150 mg, 0.4417 mmol) and 2,3,4-trifluorophenol (130.8 mg, 0.8834 mmol) are added to a vial, and the sealed mixture is heated with stirring at 140° C. for 23 h. Silica gel column chromatography (MeOH:CH2Cl2=0.5:99.5) gives the title compound as a white solid. 1H NMR (400 MHz, CDCl3) 7.66 (3H, m), 7.24 (2H, m), 7.00 (2H, m), 3.58 (3H, s). MS (M+1): 451.08; RT=1.31 min. The IC50 determined as described in Example 6 is 100 nanomolar or less.

Workup

temperatureis heated

Sources & evidence

ORD record: ord-627d0e13b3a7471c9d319e89e1325eea
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003656B2

Reaction notes

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