2-(4-Methoxybenzylamino)-5-(2-methylthioethoxy)pyrimidine → 5-(2-(Methylthio)ethoxy)pyrimidin-2-amine

HRID 906307Notes

Reaction equation

COC1C=CC(C[NH:8][C:9]2[N:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][S:18][CH3:19])=[CH:11][N:10]=2)=CC=1>FC(F)(F)C(O)=O>[CH3:19][S:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[N:14][C:9]([NH2:8])=[N:10][CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

N-(4-Methoxybenzyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine (172.4 mg) was dissolved in trifluoroacetic acid (3 mL) at room temperature, and the solution was stirred at 60° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative silica gel thin layer chromatography (chloroform: methanol=15:1) to obtain 5-[2-(methylthio)ethoxy]pyrimidin-2-amine (34 mg, 18% in 2 steps) as colorless amorphous solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe resulting residue was purified by preparative silica gel thin layer chromatography (chloroform: methanol=15:1)

Sources & evidence

ORD record: ord-f4f42107a4bb4fa69deb9f8b52274881
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012989B2

Reaction notes

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