Dimethylamine → HCID 23630299, compound

HRID 546556Notes

Reaction equation

HRID 546556 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=O)[O:28]C4C=CC=CC=4)[N:21]=3)[C:12]2=[O:36])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:37][NH:38][CH3:39]>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=[O:28])[N:38]([CH3:39])[CH3:37])[N:21]=3)[C:12]2=[O:36])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 57625978HCID 57625978, compound

Product 1

HCID 23630299HCID 23630299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 70 mg of phenyl (4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyrimidin-2-yl)carbamate obtained in stage a) below in 3 mL of tetrahydrofuran is introduced, under argon, 0.71 mL of a 2M solution of dimethylamine in tetrahydrofuran. After stirring for one hour at room temperature, the reaction medium is concentrated under reduced pressure and the residue is purified by chromatography on a column of silica, eluting with a dichloromethane/acetonitrile/methanol mixture (98/1/1 by volume) to give 20 mg of 3-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyrimidin-2-yl)-1,1-dimethylurea in the form of a white powder, the characteristics of which are as follows:

Workup

  1. concentrationthe reaction medium is concentrated under reduced pressure
  2. customthe residue is purified by chromatography on a column of silica
  3. washeluting with a dichloromethane/acetonitrile/methanol mixture (98/1/1 by volume)

Sources & evidence

ORD record
ord-1d70e10a083c497d841eb4d2ac0a94f7
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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