Water → 2-(5-methyl-[1,4]oxazepane-4-yl)-3-methyl-6-pyrimidin-4-yl-3H-pyrimidin-4-one

HRID 515446Notes

Reaction equation

Cl.[CH3:2][CH:3]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5][NH:4]1.Cl[C:11]1[N:16]([CH3:17])[C:15](=[O:18])[CH:14]=[C:13]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][N:20]=2)[N:12]=1.C(N(CC)CC)C.O>O1CCCC1>[CH3:2][CH:3]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:11]1[N:16]([CH3:17])[C:15](=[O:18])[CH:14]=[C:13]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][N:20]=2)[N:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 5-methyl-[1,4]oxazepane hydrochloride (0.08 g, 0.50 mmol) and 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (0.09 g, 0.40 mmol) in tetrahydrofuran (2 mL) in a sealed tube was added triethylamine (0.14 mL) at room temperature. The mixture was heated to 150° C. under microwave irradiation and stirred for 30 min. After cooling to room temperature, the reaction mixture was poured into water and extracted with chloroform. The extracts were dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel (chloroform/methanol=10/1 as an eluant) to yield 2-(5-methyl-[1,4]oxazepane-4-yl)-3-methyl-6-pyrimidin-4-yl-3H-pyrimidin-4-one (0.03 g, 0.09 mmol, 22%) as a white solid.

Workup

temperatureAfter cooling to room temperature
extractionextracted with chloroform
dry with materialThe extracts were dried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by flash column chromatography on silica gel (chloroform/methanol=10/1 as an eluant)

Sources & evidence

ORD record: ord-4b6330ff36e24718bf1946671bb84dc0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108957B2

Reaction notes

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