N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide → 1-[2-(Methylthio)pyrimidin-4-yl]-2-phenylethanone

HRID 2214782Notes

Reaction equation

[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CON(C)[C:13]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1)=[O:14]>C1COCC1>[CH3:22][S:21][C:17]1[N:16]=[C:15]([C:13](=[O:14])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:20]=[CH:19][N:18]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of benzylmagnesium chloride (4.7 mL, 9.38 mmol, 2 equiv) was added to a solution of N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide (1–2, 1.0 g, 4.7 mmol, 1 equiv) in THF (25 mL) cooled to −78° C. The reaction solution was allowed to warm to 0° C. and partitioned between ethyl acetate (2×100 mL) and brine. The organic extracts were combined, dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography. Elution with CH2Cl2 to 15% EtOAc/CH2Cl2 provided 1-[2-(methylthio)pyrimidin-4-yl]-2-phenylethanone (3-1) as a pale yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.73 (d, 1H, J=5 Hz), 7.52 (d, 1H, J=5 Hz), 7.25–7.37 (m, 5H), 4.48 (s, 2H), 2.66 (s, 3H).

Workup

temperatureto warm to 0° C.
custompartitioned between ethyl acetate (2×100 mL) and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by flash column chromatography
washElution with CH2Cl2 to 15% EtOAc/CH2Cl2

Sources & evidence

ORD record: ord-0ee1fa10c02845848a5c9c7273884c62
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109204B2

Reaction notes

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