Phenylacetylene → 2-(4-Methylphenyl)-9-phenylethynyl-2,6-dihydro[1,2,4]triazolo[4,3-c]-quinazoline-3,5-dione

HRID 2406206Notes

Reaction equation

[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[N:14]3[C:21](=[O:31])[N:22]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[N:23]=[C:13]3[C:12]=2[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CCN(CC)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:30][C:27]1[CH:28]=[CH:29][C:24]([N:22]2[C:21](=[O:31])[N:14]3[C:15](=[O:20])[NH:16][C:17]4[CH:18]=[CH:19][C:10]([C:8]#[C:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[CH:11][C:12]=4[C:13]3=[N:23]2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of phenylacetylene (15.0 μg, 0.137 mmol) and 8a (25.3 mg, 0.0682 mmol) in a mixture of 2 mL of DMF and 1 mL of NEt3, was added Pd(OAc)2 (1.53 mg, 6.82 μmol) and triphenylphosphine (3.57 mg, 13.6 μmol) in a seal tube. The tube was sealed under argon and the mixture was stirred at 100° C. for 18 h. 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 13a as a white solid (14 mg, 70%). mp: >300° C. (decomp.),

Workup

customThe tube was sealed under argon
temperatureThe mixture was 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-c22a41c83fcf41578a4aafa125611a47
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809355B2

Reaction notes

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