Dimethylamine, hydrochloride → HCID 59514518, compound

HRID 2422139Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:6](Cl)=[N:7][C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[N:9][C:10]=1[Cl:11].[CH:24]([N:27](CC)[CH:28](C)C)(C)C.Cl.CNC>CN(C=O)C>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:10]([Cl:11])=[N:9][C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[N:7][C:6]=1[N:27]([CH3:28])[CH3:24]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of methyl[4,6-dichloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (0.5 g, 1.40 mmol) in anhydrous DMF (5 mL) at room temperature under Ar atmosphere was added N,N-diisopropylethylamine (0.0.54 mL, 3.09 mmol) and dimethylamine hydrochloride (0.126 g, 1.54 mmol). The resulting solution was stirred at 85° C. for 16 hours at which time the reaction mixture was concentrated to dryness and the residue chromatographed over silica gel eluting with 50% EtOAc in n-hexane to give methyl[4-chloro-6-(dimethylamino)-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (0.505 g, 99% yield) as a brown oil.

Workup

concentrationwas concentrated to dryness
customthe residue chromatographed over silica gel eluting with 50% EtOAc in n-hexane

Sources & evidence

ORD record: ord-e4ff82b1de0a4e81aa0115f808c94d1f
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960393B2

Reaction notes

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