N,N'-Dimethylethylenediamine → 2-(4-Methoxybenzylamino)-5-(2-methylthioethoxy)pyrimidine

HRID 906306Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[CH3:18][S:19][CH2:20][CH2:21][OH:22].CNCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:5]2[N:4]=[CH:3][C:2]([O:22][CH2:21][CH2:20][S:19][CH3:18])=[CH:7][N:6]=2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 110 °C

Procedure

5-Bromo-N-(4-methoxybenzyl)pyrimidin-2-amine (300 mg, 1.02 mmol) was suspended in toluene (20 mL), the suspension was added with cuprous iodide (200 mg, 1.05 mmol), 2-methylthioethanol (1.06 g, 11.5 mmol), N,N′-dimethylethylenediamine (0.83 g, 9.42 mmol) and cesium carbonate (400 mg, 1.22 mmol), and the mixture was stirred at 110° C. for 66 hours in an argon atmosphere. The reaction mixture was separated by silica gel column chromatography (ethyl acetate), and then purified by preparative silica gel thin layer chromatography (hexane:ethyl acetate=1:1) to obtain N-(4-methoxybenzyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine (172.4 mg) as colorless amorphous solid.

Workup

customThe reaction mixture was separated by silica gel column chromatography (ethyl acetate)
custompurified by preparative silica gel thin layer chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-3e418b04711245be8fb66ffc1a16de44
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012989B2

Reaction notes

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