Tri-o-tolylphosphine → N-[3-[2-[6-(Methylamino)-9H-purine-9-yl]ethenyl]-4-methylphenyl]-3-(trifluoromethyl)benzamide

HRID 655792Notes

Reaction equation

[CH3:1][NH:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[CH:12]=[CH2:13].I[C:15]1[CH:16]=[C:17]([NH:22][C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH:18]=[CH:19][C:20]=1[CH3:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)C(C)C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C=O)C>[CH3:21][C:20]1[CH:15]=[CH:16][C:17]([NH:22][C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=2)=[CH:18][C:19]=1/[CH:13]=[CH:12]/[N:7]1[CH:6]=[N:5][C:4]2[C:8]1=[N:9][CH:10]=[N:11][C:3]=2[NH:2][CH3:1]

Participants

Conditions

Temperature: 110 °C

Procedure

A pressure tube was charged with N-methyl-9-vinyl-9H-purin-6-amine (0.088 g, 0.5 mmol), N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide (0.20 g, 0.5 mmol), palladium acetate (0.05 eq), tri-(o-tolyl)phosphine (0.1 eq), and DMF (2 ml). The resulting solution was degassed by bubbling N2 for 10 minutes. N,N-Diisopropylethylamine (0.19 g, 1.5 mmol) was added and this solution was stirred at 110° C. for 15 h. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated on a rotavap, and then subjected to silica gel column chromatography (5% methanol/methylene chloride) yielding the desired product: MS [M+H]+ 453; m.p. 201° C.

Workup

customThe resulting solution was degassed
customby bubbling N2 for 10 minutes
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated on a rotavap

Sources & evidence

ORD record: ord-cfddeecaa28b473484936fbc920a57e3
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071609B2

Reaction notes

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