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

HRID 586290Notes

Reaction equation

HRID 586290 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 of Example 20. Purification by chromatography (silica gel, 20% isohexane/CH2Cl2) gave 2-chloro-4-(2-fluoro-5-nitrophenyl)-pyrimidine as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.40 (1H, dd, J 10, 9 Hz), 7.85 (1H, dd, J 5, 2 Hz), 8.38-8.43 (1H, m), 8.77 (1H, d, J 6), 9.16 (1H, q, J 3 Hz).

Workup

  1. customPurification by chromatography (silica gel, 20% isohexane/CH2Cl2)

Sources & evidence

ORD record
ord-e92cbd0e880a435b812323d0b7254198
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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