Sodium hydride → 4-(1-(4-Bromophenyl)ethoxy)pyrimidine

HRID 1501226Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-(4-bromophenyl)ethanol (1 g, 5 mmol) in 20 mL of anhydrous N,N-dimethylformamide was added sodium hydride (0.36 g, 15 mmol) at room temperature and then stirred for 1 hour, 4-chloropyrimidine hydrochloride (1 g, 6 mmol) was added, and then heated at 100° C. for 12 hours. The reaction mixture was concentrated, the residue was purified by chromatography with petroleum/ethyl acetate=1:1 to afford 4-(1-(4-bromophenyl)ethoxy)pyrimidine (1.2 g, 86% yield). LRMS (M+H+) m/z: calcd for 278.01. found 278. 1H NMR (300 MHz, CD3OD) δ 8.65 (s, 1H), 8.42 (d, J=6.0 Hz, 1H), 7.48 (d, J=8.4 Hz, 2H), 7.35 (d, J=8.4 Hz, 2H), 6.92 (dd, J=6.0 and 1.2 Hz, 1H), 6.26 (q, J=6.6 Hz, 1H), 1.64 (d, J=6.6 Hz, 3H).

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by chromatography with petroleum/ethyl acetate=1:1

Sources & evidence

ORD record: ord-47f9b67e606f42b19cd98df63523e020
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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