Methyl iodide → 1-Methyl-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-2-(nitroamino)-4(1H)-pyrimidinone

HRID 705815Notes

Reaction equation

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

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-2-(nitroamino)-4(1H)-pyrimidinone (200 mg, 0.719 mmol) in chloroform (5 mL) was mixed with methyl iodide (0.054 mL, 0.863 mmol). The reaction mixture was stirred at 23° C. overnight. Purification via a reverse phase Biotage then provided the title compound (35 mg, 16.66% yield). LCMS: rt=1.62 min, [M+H+]=293.1

Workup

customPurification via a reverse phase Biotage

Sources & evidence

ORD record: ord-1a209a9507834c5ab3e9d4b39a75922d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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