1-(Bromomethyl)-4-chlorobenzene → 2,4-Dichloro-6-[2-(4-chlorophenyl)ethyl]pyrimidine

HRID 1822775Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[N:15]=[C:14]([Cl:16])[CH:13]=[C:12]([CH3:17])[N:11]=1.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>O1CCCC1>[Cl:9][C:10]1[N:15]=[C:14]([Cl:16])[CH:13]=[C:12]([CH2:17][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([Cl:18])=[CH:20][CH:21]=2)[N:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium diisopropylamide (11 mL, 2 M solution in heptane/tetrahydrofuran/ethylbenzene) was added dropwise over 5 min to a solution of 2,4-dichloro-6-methylpyrimidine (3.0 g) in tetrahydrofuran (20 mL) at −78° C. under nitrogen. The reaction was stirred at −78° C. for 30 minutes. 4-Chlorobenzylbromide (4.4 g) was dissolved in tetrahydrofuran (5 mL) and added dropwise over 5 minutes. The reaction was stirred at −78° C. for 30 min, allowed to warm to rt and stirred at rt for 16 h. Solvent was removed under vacuum. The residue was purified by column chromatography (5% ethyl acetate in hexanes) to afford 2,4-dichloro-6-[2-(4-chlorophenyl)ethyl]pyrimidine, (2.8 g).

Workup

additionadded dropwise over 5 minutes
stirringThe reaction was stirred at −78° C. for 30 min
temperatureto warm to rt
stirringstirred at rt for 16 h
customSolvent was removed under vacuum
customThe residue was purified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-358f02d77de547a09e8a0631f27fc751
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037916B2

Reaction notes

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