Methyltriphenylphosphonium iodide → (R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-5'-isopropenyl-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 1480006Notes

Reaction equation

[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:28]([C:35]1[N:40]=[N:39][C:38]([N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[N:51][C:50]([C:53](=O)[CH3:54])=[CH:49][N:48]=3)[C@H:43]([CH3:56])[CH2:42]2)=[C:37]([CH3:57])[C:36]=1[CH3:58])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH2:28]([C:35]1[N:40]=[N:39][C:38]([N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[N:51][C:50]([C:53]([CH3:2])=[CH2:54])=[CH:49][N:48]=3)[C@H:43]([CH3:56])[CH2:42]2)=[C:37]([CH3:57])[C:36]=1[CH3:58])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Methyltriphenylphosphonium iodide (410 mg, 1.010 mmol) is added to THF (5.5 mL) and cooled to 5° C. Potassium tert-butoxide (1.1 mL, 1M in THF, 1.1 mmol) is added dropwise and the reaction is stirred for 30 min. 1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl]-ethanone (350 mg, 0.841 mmol) in THF (1.5 mL) is added to the reaction. The reaction is allowed to stir 1 h at 5° C., and then the ice bath is removed and the reaction is allowed to stir an additional 16 h at room temperature. Remove THF in vacuo. The residue is purified by flash chromatography on silica gel (60-90% EtOAc/heptane) to afford the title compound (130 mg, 37%).

Workup

stirringto stir 1 h at 5° C.
customthe ice bath is removed
stirringto stir an additional 16 h at room temperature
customThe residue is purified by flash chromatography on silica gel (60-90% EtOAc/heptane)

Sources & evidence

ORD record: ord-a3b357ef1f0748fcbd7322330986b160
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409871B2

Reaction notes

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