Formic Acid → N-(4-((4-(Pyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)formamide

HRID 1282136Notes

Reaction equation

C(O[C:5](=[O:7])C)(=O)C.C(O)=O.C(OC(=O)C)=O.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:32]3[N:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[CH2:28][CH2:27]2)=[CH:21][CH:20]=1>C(Cl)Cl>[N:33]1[CH:34]=[CH:35][CH:36]=[N:37][C:32]=1[N:29]1[CH2:30][CH2:31][N:26]([CH2:25][C:22]2[CH:23]=[CH:24][C:19]([CH2:18][NH:17][CH:5]=[O:7])=[CH:20][CH:21]=2)[CH2:27][CH2:28]1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of acetic anhydride (0.30 ml) and formic acid (0.13 ml) was stirred at 50-60° C. for 1 hr. To the obtained acetic formic anhydride was added a solution of 2-(4-(4-(aminomethyl)phenylmethyl)piperazin-1-yl)pyrimidin (0.42 g) in methylene chloride (10 ml) under ice-cooling and the mixture was stirred at 5-10° C. for 2 hr. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1) to give a yellow oil. (0.46 g). The obtained yellow oil was crystallized from ethyl acetate/diisopropyl ether to give the title compound (0.45 g) as pale-yellow crystals, m.p.=97-98° C.

Workup

temperaturecooling
stirringthe mixture was stirred at 5-10° C. for 2 hr
concentrationThe reaction mixture was concentrated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1)
customto give a yellow oil
customThe obtained yellow oil was crystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record: ord-44a20364598f4cb685675335d0fb1d01
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455528B1

Reaction notes

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