Stannane, tributyl(phenylmethyl)- → 9-Benzyl-2-(4-methylphenyl)-2,6-dihydro[1,2,4]triazolo[4,3-c]quinazoline-3,5-dione

HRID 2406208Notes

Reaction equation

[CH2:1]([Sn](CCCC)(CCCC)CCCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:22]1[CH:31]=[CH:30][C:29]2[NH:28][C:27](=[O:32])[N:26]3[C:33](=[O:43])[N:34]([C:36]4[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=4)[N:35]=[C:25]3[C:24]=2[CH:23]=1>CN(C=O)C.CCN(CC)CC.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>[CH2:1]([C:22]1[CH:31]=[CH:30][C:29]2[NH:28][C:27](=[O:32])[N:26]3[C:33](=[O:43])[N:34]([C:36]4[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=4)[N:35]=[C:25]3[C:24]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of benzyltributyltin (69 mg, 0.184 mmol) and 8a (19.5 mg, 0.0525 mmol) in a mixture of 2 mL of DMF and 1 mL of NEt3, was added Pd(PPh3)4 (6.0 mg, 5.3 μmol). The seal tube was sealed under argon and the mixture was stirred at 110° C. for 18 h. The reaction the mixture was cooled and concentrated to dryness in vacuo and the crude product was purified by chromatography on a silica gel column. Elution with n-heptane/EtOAc (2:1) as eluent yielded 16a as a white solid (13 mg, 65%). mp: 299° C.,

Workup

customThe seal tube was sealed under argon
customThe reaction the mixture
temperaturewas cooled
concentrationconcentrated to dryness in vacuo
customthe crude product was purified by chromatography on a silica gel column
washElution with n-heptane/EtOAc (2:1) as eluent

Sources & evidence

ORD record: ord-0ea7e6d8e72946018e08c98e6acb2320
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809355B2

Reaction notes

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