4-methoxyphenyl methyl

Six protective groups for alcohols, which may be removed successively and selectively, have been listed by E.J. Corey (1972B). A hypothetical hexahydroxy compound with hydroxy groups 1 to 6 protected as (1) acetate, (2) 2,2,2-trichloroethyl carbonate, (3) benzyl ether, (4) dimethyl-t-butylsilyl ether, (5) 2-tetrahydropyranyl ether, and (6) methyl ether may be unmasked in that order by the reagents (1) KjCO, or NH, in CHjOH, (2) Zn in CHjOH or AcOH, (3) over Pd, (4) F", (5) wet acetic acid, and (6) BBrj. The groups may also be exposed to the same reagents in the order A 5, 2, 1, 3, 6. The (4-methoxyphenyl)methyl group (=MPM = p-methoxybenzyl, PMB) can be oxidized to a benzaldehyde derivative and thereby be removed at room temperature under neutral conditions (Y- Oikawa, 1982 R. Johansson, 1984 T. Fukuyama, 1985). 

II. 5-Bis(4-methoxyphenyl)methyl Thioether RSCH(C6H4-4-OCH3)2 (Chart 7)... 

S-Diphenylmethyl, 466 S-Bis(4-methoxyphenyl)methyl, 467 S-5-Dibenzosuberyl, 468 S-Triphenylmethyl, 468 S-Diphenyl-4-pyridylmethyl, 469 S-Phenyl, 469... 

Treatment of 2-[(4-methoxyphenyl)methyl] derivative of 2,3,6,7-tetra-hydro-l//,5//-pyrido[3,2,l-//]quinazoline-l,3-diones with (NH4)2Ce(N03)g afforded 2-unsubstituted derivatives. A 2-unsubstituted derivative was N-alkylated with 4-methoxybenzyl chloride in DMF in the presence of K2CO3 at 50 °C (01MIP22). 

Chemical Name N-[(4-Methoxyphenyl)methyl] -N,N -dimethyl-N-2-pyrimidinyl-1,2-ethane-diamine monohydrochloride... 

CN A-[(4-methoxyphenyl)methyl]-A ,7/ -dimethyl-A-2-pyridinyl-1,2-ethanediamine monohydrochloride... 

PREPARATION OF SECONDARY AMINES FROM PRIMARY AMINES VIA 2-NITROBENZENESULFONAMIDES N-(4-METHOXYBENZYL)-3-PHENYLPROPYLAMINE [Benzenepropanamine, N-[(4-methoxyphenyl)methyl]-]... 

Methoxyphenyl)methyl 6/FAmino-6at-methylpcnicillanate (3, R2 = 4-CH1OCt,H4CH R3 = CH3) Typical Hydrolysis Procedure4 ... 

A solution of 2.58 g (5.9 mmol) of (4-methoxyphenyl)methyl 6/J-benzylideneamino-6a-methylpenicillanate (2. R1 = C6H5 R2 = 4-CH3OC6H4CH2 R3 = CH3) in 75 mL of ethyl acetate is stirred at 20 C. 1.61 g (8.5 mmol) of 4-methyl benzenesulfonic acid and 1.61 mL(90 mmol) of water are added. A white solid starts to precipitate almost instantaneously. The reaction is allowed to proceed for 3 h before the white solid is filtered off and dried in vacuo to give 2.47 g (80%) of a salt. The latter is treated with aq NaHC03 to liberate the free amine which is recrystallized from ethyl acetate/hexane yield 1.33 g (65%) mp 84-87 °C. 

The first detailed paper in the field of the pharmacology of the pyrido-[l,2-o]pyrimidines was a study on the histamine-liberating and nonspecific spacmolytic activity of 2-(2-dimethylaminoethyl)-3-(4-methoxyphenyl-methyl)-4-oxo-4//-py rido [ 1,2-a] pyrimidine.383... 

Methoxyphenyl Methyl Phenyl TeUnronium Iodide6 1.5 g (4.8 mmol) of 4-methoxyphenyl phenyl tellurium and 6.8 g (3 ml 48 mmol) of methyl iodide arc mixed and kept at 20° for 48 h. Diethyl ether is added to the mixture which is allowed to stand for 12 h. The mixture is then filtered and the solid dried yield 2.1 g (94%) m.p. 56°. 

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