2-Dimethylaminopyridine → HCID 86625979, compound

HRID 658271

Reaction equation

HRID 658271 reaction equation
[C:1]1([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[CH2:32]([NH:38][C:39]([NH:41][C:42]1[CH:47]=[CH:46][N:45]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]O)[C:44](=[O:55])[N:43]=1)=[O:40])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(Cl)Cl>[CH2:32]([NH:38][C:39](=[O:40])[NH:41][C:42]1[CH:47]=[CH:46][N:45]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][O:21][C:20](=[O:22])[CH2:19][CH2:18][CH2:17][C:1]2[C:14]3[C:15]4=[C:16]5[C:11](=[CH:12][CH:13]=3)[CH:10]=[CH:9][CH:8]=[C:7]5[CH:6]=[CH:5][C:4]4=[CH:3][CH:2]=2)[C:44](=[O:55])[N:43]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 769771-Pyrenebutanoic acidHCID 68972726HCID 68972726, compound

Product 1

HCID 86625979HCID 86625979, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of pyrene butyric acid (commercially available) (0.05 g, 0.17 mmol) in CH2Cl2 (5 ml) was added at 0° C., dicyclohexylcarboimide (0.044 g, 0.210 mmol) and dimethylaminopyridine (4 mg). The mixture was stirred for 1 h. 1-Hexyl-3-[1-(6-hydroxy-hexyl)-2-oxo-1,2-dihydro-pyrimidinyl]-urea) (J) was then added to the mixture and the solution was stirred at room temperature for 16 h. The solid was filtered off and the filtrate washed with water (2×10 ml) then saturated sodium chloride solution (5 ml). The organic phase was then dried (MgSO4) and the solvent evaporated in vacuo. The crude solid was purified using flash silica gel chromatography using a gradient: 1) (CHCl3) 2) (CHCl3/EtOAc, 5:1) and 3) (CHCl3/EtOAc/Et3N, 5:1:0.2). 4-Pyren-1-yl-butyric acid 6-[4-(3-hexyl-ureido)-2-oxo-2H-pyrimidin-1-yl]-hexyl ester (K) was obtained as a yellow solid (0.025 mg, 23%).

Workup

  1. stirringthe solution was stirred at room temperature for 16 h
  2. filtrationThe solid was filtered off
  3. washthe filtrate washed with water (2×10 ml)
  4. dry with materialThe organic phase was then dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude solid was purified

Sources & evidence

ORD record
ord-ba111a3cf5044031ad59db91a39d0426
Source dataset
uspto-grants-2011_12
Patent number
US08076426B2

Linked notes

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