2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → HCID 17839507, compound

HRID 600134Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN1C(=O)N(C)CCC1.I[C:38]1[C:51](I)=[CH:50][C:49]2[C:40](=[C:41]([CH2:56][CH2:57][CH3:58])[C:42]3[C:47]([C:48]=2[CH2:53][CH2:54][CH3:55])=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:39]=1>C1COCC1.Cl[Cu]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:44]3[C:45](=[CH:46][C:47]4[C:42]([CH:43]=3)=[C:41]([CH2:56][CH2:57][CH3:58])[C:40]3[C:49](=[CH:50][CH:51]=[CH:38][CH:39]=3)[C:48]=4[CH2:53][CH2:54][CH3:55])[C:15]([C:16]3[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][CH:21]=3)=[C:14]3[C:9]=2[CH2:10][CH2:11][CH2:12][CH2:13]3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1,8-Bis(p-bromophenyl)-1,7-octadiyne (0.191 g, 0.459 mmol) was added at −78° C. to a THF solution of bis(η5-cyclopentadienyl)dibutylzirconium in THF, which was prepared from bis(η5-cyclopentadienyl)dichlorozirconium (0.161 g, 0.551 mmol) and n-butyl lithium (0.7 ml, 1.6 M, 1.1 mol/l). The mixture was then allowed to stand at room temperature for an hour. CuCl (0.095 g, 0.964 mmol), DMPU (0.17 ml, 1.38 mmol) and 2,3-diiodo-9,10-dipropylanthracene (0.236 g, 0.459 mmol) were added to the mixture. After heating at 50° C. for an hour, the solvent in the mixture was removed in vacuum. Column chromatography (chloroform) was performed. By recrystallization in chloroform/methanol, the title compound (0.177 g) was obtained as orange red. The isolation yield was 57%.

Workup

waitto stand at room temperature for an hour
customthe solvent in the mixture was removed in vacuum
customBy recrystallization in chloroform/methanol

Sources & evidence

ORD record: ord-1d7fe49e629947c59c7710c8376425d1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07901594B2

Reaction notes

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