Phenol → HCID 57597382, compound

HRID 1786871Notes

Reaction equation

[Si]([O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[N:20]([CH2:21][CH3:22])[C:19]2[C:18](OC3C=CC=CC=3)=[N:17][CH:16]=[N:15][C:14]=2[CH:13]=1)(C(C)(C)C)(C)C.[CH3:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][C:37]=1[O:38][C:39]1[CH:40]=[N:41][C:42]([CH3:45])=[CH:43][CH:44]=1)[NH2:34].Cl.N1C=CC=CC=1.C1(O)C=CC=CC=1>ClCCl>[CH2:21]([N:20]1[C:19]2[C:18]([NH:34][C:33]3[CH:35]=[CH:36][C:37]([O:38][C:39]4[CH:40]=[N:41][C:42]([CH3:45])=[CH:43][CH:44]=4)=[C:31]([CH3:30])[CH:32]=3)=[N:17][CH:16]=[N:15][C:14]=2[CH:13]=[C:12]1/[CH:11]=[CH:10]/[CH2:9][OH:8])[CH3:22]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-((1E)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-propenyl)-5-ethyl-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidine (78 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (61.2 mg), pyridine hydrochloride (26 mg) and phenol (122 mg) was stirred with heating at 120° C. for 16 hrs. After cooling to room temperature, the mixture was diluted with dichloromethane (30 mL), and washed with saturated aqueous sodium hydrogen carbonate (20 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by basic silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→80:20) to give the title compound (32 mg) as a powder.

Workup

temperatureAfter cooling to room temperature
washwashed with saturated aqueous sodium hydrogen carbonate (20 mL)
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was separated
custompurified by basic silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→80:20)

Sources & evidence

ORD record: ord-eb44393fedd44638a22d225f917392a8
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507740B2

Reaction notes

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