4-Fluorobenzyl bromide → 2-(3,5-Dichlorophenyl)-4-[(4-fluorobenzyl)oxy]-6-isopropylpyrimidine

HRID 29903Notes

Reaction equation

HRID 29903 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([OH:15])[CH:12]=[C:11]([CH:16]([CH3:18])[CH3:17])[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[N:14]=[C:13]([O:15][CH2:24][C:23]3[CH:26]=[CH:27][C:20]([F:19])=[CH:21][CH:22]=3)[CH:12]=[C:11]([CH:16]([CH3:18])[CH3:17])[N:10]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 178439458HCID 178439458, compound2×

Product 1

HCID 102498492-(3,5-Dichlorophenyl)-4-[(4-fluorobenzyl)oxy]-6-isopropylpyrimidine

Procedure

The title compound was prepared from 2-(3,5-dichloro-phenyl)-6-isopropyl-pyrimidin-4-ol (which was obtained in Intermediate 6) and 4-fluorobenzyl bromide according to Method A; 1H NMR (DMSO-d6, 300 MHz) δ 1.27 (d, J=6.8 Hz, 6H), 2.90-3.10 (m, 1H), 5.54 (s, 2H), 6.88 (s, 1H), 7.24 (t, J=8.9 Hz, 2H), 7.57 (d, J=8.9, 8.5 Hz, 2H), 7.81 (s, 1H), 8.33 (s, 2H); LC retention time 4.45 min; MS: m/z (ESI) 391 (M+H).

Sources & evidence

ORD record
ord-564c311f8b8340389fe9e122cf634a45
Source dataset
uspto-grants-2008_09
Patent number
US07423044B2

Reaction notes

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