HCID 60204331, compound → HCID 60204330, compound

HRID 507536Notes

Reaction equation

HRID 507536 reaction equation
[CH3:1][C:2]1([CH3:30])[N:6]([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][C:18]4[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][C:19]=4[CH:20]=3)[CH:13]=[CH:12][N:11]=2)[C:5](=[O:28])[NH:4][C:3]1=[O:29].[H][H]>CO.[Pd]>[CH3:1][C:2]1([CH3:30])[N:6]([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][C:18]4[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:19]=4[CH:20]=3)[CH:13]=[CH:12][N:11]=2)[C:5](=[O:28])[NH:4][C:3]1=[O:29]

Participants

5

Reactant 2

HCID 60204331HCID 60204331, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 60204330HCID 60204330, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5,5-Dimethyl-1-(2-(4-(5-nitrobenzothiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazo-lidine-2,4-dione (1.2 g, 2.82 mmol) was suspended in methanol (120 mL), 20% palladium on carbon (120 mg) was added, and the mixture placed on a Parr shaker under 50 psi of hydrogen gas for a total of 7 days. The reaction mixture was filtered through a thick bed of celite and washed with methanol (5×50 mL) to give a bright yellow solution. The crude material was purified by flash chromatography (MeOH/DCM) to give the title compound as a light yellow powder (300 mg, 63%). MS (M+H)+ 411.

Workup

  1. filtrationThe reaction mixture was filtered through a thick bed of celite
  2. washwashed with methanol (5×50 mL)
  3. customto give a bright yellow solution
  4. customThe crude material was purified by flash chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-bfedba7a31644061abee07952065bbb4
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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