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

HRID 2353330Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

Colorless amorphous solid of 2-(4-methoxybenzylamino)-5-(2-methylthioethoxy)pyrimidine (172 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 to obtain 2-amino-5-(2-methylthioethoxy)pyrimidine (34 mg, 18% for 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

Sources & evidence

ORD record: ord-17995b0e0c68469097ffcab6f2285569
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750019B2

Reaction notes

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