2,4-Dichloropyrimidine → 2-Chloro-4-(2-fluoro-5-nitrophenyl)pyrimidine

HRID 1061798Notes

Reaction equation

HRID 1061798 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1>>[Cl:1][C:2]1[N:7]=[C:6]([C:11]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=2[F:9])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 222853262-Chloro-4-(2-fluoro-5-nitrophenyl)pyrimidine

Procedure

2,4-Dichloropyrimidine (2.0 g, 13 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.9 g, 15 mmol) using the method in Example 14 part a). Purification by chromatography on silica gel eluting with dichloromethane containing 20% isohexane gave 2-chloro-4-(2-fluoro-5-nitro-phenyl)pyrimidine as a white solid: δH (400 MHz, CDCl3) 7.40 (1H, dd, J 10 and 9), 7.85 (1H, dd, J 5 and 2), 8.38-8.43 (1H, m), 8.77 (1H, d, J 6), 9.16 (1H, q, J 3).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 20% isohexane

Sources & evidence

ORD record
ord-c86b677abaa542799f591bc600093922
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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