2-Ethylaminoethyldimethylamine → N-[2-(dimethylamino)ethyl]-N-ethyl-4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]benzamid

HRID 422057Notes

Reaction equation

HRID 422057 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:23]=[CH:22]C(C(O)=O)=[CH:17][CH:16]=3)[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:24].[CH3:25][N:26]([CH3:32])[CH2:27][CH2:28][NH:29][CH2:30][CH3:31].[OH:33]N1C2C=CC=CC=2N=N1.CCN=C=NC[CH2:49][CH2:50][N+](C)(C)C.[I-]>ClC(Cl)C.CN(C)C=O>[CH3:25][N:26]([CH3:32])[CH2:27][CH2:28][N:29]([CH2:49][CH3:50])[C:30](=[O:33])[C:31]1[CH:22]=[CH:23][C:15]([C:10]2[NH:11][C:12](=[O:14])[N:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([CH3:24])[CH:4]=3)[CH:9]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 671622-EthylaminoethyldimethylamineHCID 757711-HydroxybenzotriazoleHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 1359001814-(6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid

Product 1

HCID 135589873N-[2-(dimethylamino)ethyl]-N-ethyl-4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]benzamidYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid (16.9 mg, 48 μmol) and N,N-dimethyl-N′-ethylethylenediamine (4.6 mg, 40 μmol) in dichloroethane (1.25 mL) and N,N-dimethylformamide (0.79 mL) was added 1-hydroxybenzotriazole (6.8 mg, 50 μmol) followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (17.8 mg, 60 μmol). The resultant mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated in vacuo. Purification of the residue by HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) followed by concentration in vacuo gave the title compound N-[2-(dimethylamino)ethyl]-N-ethyl-4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]benzamid (3 mg, 20%). 1H NMR (400 MHz, d6-DMSO): 8.21 (m, 3H), 7.97 (s, 1H), 7.87 (dd, 1H), 7.49 (m, 3H), 6.90 (d, 1H), 3.41 (m, 4H), 2.33 (m, 2H), 2.22 (m, 6H), 1.97 (s, 3H), 1.10 (m, 3H); MS (EI) for C24H28N4O3: 421 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification of the residue by HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)
  3. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-adc760f08dbb40c8ad59665e4720e138
Source dataset
uspto-grants-2012_01
Patent number
US08101625B2

Reaction notes

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