1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 1-(2-{4-[5-(2-Ethylphenylthio)thiophen-2-yl]pyrimidin-2-ylamino}ethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 507582Notes

Reaction equation

I[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][N:16]3[C:20]([CH3:22])([CH3:21])[C:19](=[O:23])[NH:18][C:17]3=[O:24])[N:8]=2)=[CH:4][CH:3]=1.[CH2:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[SH:33])[CH3:26].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(O[K])(C)(C)C>C1(C)C=CC=CC=1.C(O)(C)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][N:16]3[C:20]([CH3:22])([CH3:21])[C:19](=[O:23])[NH:18][C:17]3=[O:24])[N:8]=2)=[CH:4][CH:3]=1)[CH3:26]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 1-{2-[4-(5-iodothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethyl-imidazolidine-2,4-dione (50 mg, 0.109 mmol) and 0.060 mL (0.44 mmol) of 2-ethylthiophenol in 2 mL toluene was treated with 3 mg of Pd2dba3 (0.003 mmol), 3 mg of Xantphos (0.005 mmol) and 0.22 mL of a 1 M solution of tBuOK in t-butanol. The reaction vial was sealed and heated at 110° C. in a microwave for 10 min. The crude solution was concentrated onto 5 g of silica gel and then purified by flash chromatography to give the title compound. MS (M+H)+ 468.

Workup

customThe reaction
customvial was sealed
concentrationThe crude solution was concentrated onto 5 g of silica gel
custompurified by flash chromatography

Sources & evidence

ORD record: ord-38556768d38a4675ac3811ec530d116a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786132B2

Reaction notes

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