Sodium hydride → 4-[2-(4-Tert-butylphenyl)ethoxy]-5-methoxy-6-methoxymethylpyrimidine

HRID 342508

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].Cl[C:19]1[C:24]([O:25][CH3:26])=[C:23]([CH2:27][O:28][CH3:29])[N:22]=[CH:21][N:20]=1>CN(C)C=O.ClCCl.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][O:13][C:19]2[C:24]([O:25][CH3:26])=[C:23]([CH2:27][O:28][CH3:29])[N:22]=[CH:21][N:20]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

5.4 g (0.03 mol) of 2-(4-tert-butylphenyl)ethanol were added dropwise at 50° C. to a suspension of 1.2 g (0.03 mol) of sodium hydride (60% dispersion in oil) in 50 ml of dry dimethylformamide, and the mixture was stirred until the evolution of hydrogen had ceased. The mixture was cooled to 0° C., and 4.7 g (0.025 mol) of 4-chloro-5-methoxy-6-methoxymethylpyrimidine (Coll. Czechoslov. Chem. Commun. 33, 2266 (1968)) were added. The mixture was stirred for 1 hour at room temperature and for 2 hours at 100° C. After the solvent had been stripped off, the residue was taken up in dichloromethane/water, and the organic phase was dried and evaporated on a rotary evaporator. The crude product was chromatographed on silica gel using ethyl acetate. 3.8 g (46% of theory) of 4-[2-(4-tert-butylphenyl)ethoxy]-5 -methoxy-6 -methoxymethylpyrimidine were obtained in the form of a yellow oil.

Workup

customthe organic phase was dried
customevaporated on a rotary evaporator
customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record: ord-5f15bb1b4b234011ac016c5a9a64901d
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859020

Linked notes

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