1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (4S)-4-(Propan-2-yl)-1-[5-(trifluoromethyl)pyrimidin-2-yl]imidazolidin-2-one

HRID 2401265Notes

Reaction equation

HRID 2401265 reaction equation
[CH3:1][CH:2]([C@H:4]1[CH2:8][NH:7][C:6](=[O:9])[NH:5]1)[CH3:3].Cl[C:11]1[N:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1.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.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][CH:2]([C@H:4]1[CH2:8][N:7]([C:11]2[N:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)[C:6](=[O:9])[NH:5]1)[CH3:3]

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 133170192-Chloro-5-(trifluoromethyl)pyrimidineHCID 23676156Sodium t-butoxideHCID 24808374(S)-4-Isopropylimidazolidin-2-one

Product 1

HCID 86705168(4S)-4-(Propan-2-yl)-1-[5-(trifluoromethyl)pyrimidin-2-yl]imidazolidin-2-oneYield 22%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of (4S)-4-(propan-2-yl)imidazolidin-2-one (100 mg), 2-chloro-5-trifluoromethylpyrimidine (142 mg), Pd2(dba)3 (40 mg), Xantphos (45 mg) and sodium tert-butoxide (70 mg) in toluene (2 mL) was stirred at 100° C. for 1 hr. The reaction mixture was purified by column chromatography (NH silica gel cartridge and silica gel cartridge, hexane/ethyl acetate) to afford the title compound (47 mg).

Workup

  1. customThe reaction mixture was purified by column chromatography (NH silica gel cartridge and silica gel cartridge, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3c254e06f2fc4fac804561857918016b
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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