3,5-Dimethylphenol → 2,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine

HRID 426138

Reaction equation

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

Participants

Conditions

Temperature: -40 °C

Procedure

To a stirred mixture of 2,4,6-Trichloro-5-isopropyl-pyrimidine (23.68 g, 0.105M), 3,5-dimethylphenol (12.2 g, 0.2M) in anhydrous DMF (200 ml) cooled in a dry ice-acetone bath (−40° C.) under nitrogen atmosphere, was portionwise added 60% sodium hydride (4.2 g, 0.105M). The reaction temperature was then slowly raised to room temperature during 3 hr. The reaction mixture was then diluted with ether, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a pale yellow solid. The crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:9)) to afford 28 g (90%) a white solid. m.p. 107-108° C.; 1H NMR (200 MHz, CDCl3) δ 1.40 (6H, d, J=7.0 Hz), 2.35 (6H, s), 3.58 (1H, m), 6.72 (2H, s), 6.91 (1H, s).

Workup

temperatureThe reaction temperature was then slowly raised to room temperature during 3 hr
washwashed with water twice
dry with materialdried with anhydrous magnesium sulfate
filtrationfiltered
customevaporated in vacuo
customto give a crude product as a pale yellow solid
customThe crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:9))

Sources & evidence

ORD record: ord-2a88cbafaae04e5f900b82cd3f46b648
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Linked notes

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