4-dimethylamino pyridine

Novel amine chemistry based on 4-(dimethylamino)pyridine-catalyzed acylation 98ACR494. 

R = R = H, R = -0CH2CH20H), and the hydroxy group then was acylated with 2-(dimethylamino)acetic acid in CH2CI2 in the presence of 1,3-dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine at room temperature (94EUP626378, 95USP5378720). 

The 1,5-benzoxazepinedione 1 is obtained from 2-aminophenol and the 5,5 -diphenyl ester of dithiomalonic acid in the presence of a catalytic amount of 4-(dimethylamino)pyridine.37... 

Cp pentamethylcyclopentadienyl Tmp 2,2,6,6-tetramethylpiperidine Dipp 2,6-di(iso-propyl)phenyl Trip 2,4,6-tri(iso-propyl)phenyl Mes 2,4,6-trimethylphenyl Mes 2,4,6-tri(tert-butyl)phenyl Ada adamantyl dmap 4-(dimethylamino)pyridine Tms trimethylsilyl (SiMe3)... 

Wurz RP, Lee EC, Ruble JC, Fu GC (2007) Synthesis and resolution of planar-chiral derivatives of 4-(dimethylamino)pyridine. Adv Synth Catal 349 2345-2352... 

Dimethylamino)pyridine (1, DMAP) and its analogs, particularly 4-(pyrrolidino)pyridine (2, PPY) have acquired enormous importance and utility as supemucleophilic catalysts in synthetic organic and polymer chemistry (1, 2). 

AW, Acid-washed Choi, Cholesterol DMAP, 4-(Dimethylamino)pyridine DMF, N,/V-Dimethylformamide DMTr, Di(p-niethoxyphenyl)phenyl methyl GalNAc, N-Acetylgalactosamine, 2-acetamido-2-deoxy-D-galactose HMF, 5-Hydroxymethylfur-fural, 5-(hydroxymethyl)-2-furaldehyde INOC, Intramolecular nitrile oxide-alkene cycloaddition Lea, Lewisa Lex, Lewisx MOM, Methoxymethyl MP, p-Methoxyphe-nyl MS, Molecular sieves NIS, N-Iodosuccinimide PCC, Pyridinium chlorochromate PDC, Pyridinium dichromate PMA, Phosphomolybdic acid PMB, p-Methoxybenzyl ... 

Another example has been provided by Ito et al., who described the use of methanofullerene derivatives as powerful and stable precursors for glycofullerenes.217 Their study was based on the use of [60]fullerenoacetyl chloride (227), obtained from the ferf-butyl [60]fullerenoacetate derivative 226, which had been prepared in 56% yield by treatment of corresponding stabilized sulfonium ylides 225 with C6o-218 Subsequent transformation with p-TsOH in toluene gave [60]full-erenoacetic acid, which was directly converted into the corresponding acyl chloride 227 by using thionyl chloride. Standard ester formation with methyl 2,3,4-tetra-O-benzyI -/<-d-gl ucopyranoside (228) and 4-(dimethylamino)pyridine (DMAP) afforded the desired hybrid derivative 229 in 66% yield. 

Dissolve 6 mmol of 4-(dimethylamino)pyridine in 10 ml of dry acetone (base). 

If N-succinimidyl chloroformate was used, filter out the white precipitate of 4-(dimethylamino) pyridine hydrochloride using a glass fiber filter pad. Collect the supernatant. 

Recent developments are ring-cleavage reactions of the heterocycles [R2M-SbR2]w with 4-(dimethylamino)pyridine leading to base-stabilized monomers, [L — R M-SbR, (R = Me, SiMe3 R = Me, Et, i-Bu M = A1, Ga).83,84 Reaction of [L-Al(Me2)-Sb(SiMe3)2] [L = 4-(dimethylamino)pyr-idine] with [Ni(CO)4] leads to the corresponding tricarbonyl nickel complex (Equation 4).85... 

DIBAL Diisobutylaluminum hydride DMAP 4-(dimethylamino)pyridine DME 1,2-dimethoxyethane... 

In a 250 mL round-bottomed flask equipped with a magnetic stirring bar were placed dichloromethane (54 mL), (R, R)-1,1 -bis(a-hydroxypropyl)ferroccnc (9.84 g) and a catalytic amount of 4-(dimethylamino)pyridine (39.8 mg) under nitrogen. Triethylamine (36.4mL) and acetic anhydride (12.2 mL) were... 

Wang resin was purchased from Advanced ChemTech (1% DVB, 0.70mmol/g substitution, 100-200 mash, Cat. SA5009). Anhydrous tetrahydrofuran (THF), A/A-dimcthyl-formamide (DMF), methanol, dichloromethane, pyridine, 1,1 -carbonyldiimidazole (CDI), piperazine, homopiperazine, trans-1,4-diaminocyclohexane, 4-(dimethylamino)pyridine (DMAP), succinic anhydride, diglycolic anhydride, 3-methyl-glutaric anhydride, 2-aminophenol, 2-amino-p-cresol, 2-amino-4-tert-butyl phenol, /V-methylmorpholine (NMM), triphenylphosphine, diethyl azodicarboxylate (DEAD), and trifluoroacetic acid (TFA) were purchased from Aldrich Chemical Company, Inc. and used without further purification. PyBOP was purchased from Novabiochem. 

The reaction of f)-keto esters with primary or secondary amines in the presence of a trace of 4-(dimethylamino)pyridine affords keto amides in good yields. Thus methyl acetoacetate and p-toluidine gave MeCOCT CONHCgTLtMe328. Several selective acylation reactions of amines have been described. Amines are converted into formamides... 

B. Mono(2,6-dimethoxybenzoyl)tartaric acid. In a 250-mL, three-necked, round-bottomed flask, equipped with a nitrogen inlet, a reflux condenser and a magnetic stirring bar are placed 6.1 g (18.5 mmol) of dibenzyl tartrate, 100 mL of dry dichloromethane, 4 mL (28.8 mmol) of triethylamine and 50 mg (0.4 mmol) of 4-(dimethylamino)pyridine. The stirred mixture is cooled to 0°C 3.65 g (18.2 mmol) of 2,6-dimethoxybenozyl chloride (Note 3) is added portion-wise over 1 hr. The reaction mixture is then warmed to room temperature and refluxed for 12 to 18 hr (the reaction is easily monitored by TLC). The reaction mixture is then allowed to cool down to room temperature and poured in 100 mL of water, The aqueous phase is extracted with 2 x 75 mL of dichloromethane. The organic phases are combined, dried over odium sulfate, filtered and concentrated to give a viscous oil. This is purified by... 

An enamine was trifluoromethylated with 5-salt 17 (1 equivalent) in the presence of an equimolar amount of 4-(dimethylamino)pyridine to give mono(trifluoromethyl) and di(trifluoromethyl) ketones (Eq. 23). 

Naphthol and p-hydroquinone were smoothly trifluoromethylated with 39 in the presence of 4-(dimethylamino)pyridine or pyridine (Eqs. 25, 26) as an acid trap. 

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