Phenylboronic Acid → 2,4-Dichloro-6-phenylpyrimidine

HRID 75407

Reaction equation

HRID 75407 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 2415542,4-Dichloro-6-phenylpyrimidine

Procedure

As shown in Scheme 17, reaction of 2,4,6-trichloropyrimidine (8) with phenylboronic acid occurred at position 6 of the pyrimidine ring to give 2,4-dichloro-6-phenylpyrimidine (39) as the only isolated product. This is in contrast to the amine displacement reactions of Schemes 3 and 16, which occurred largely at the 4 position. Subsequent reaction with bridged C5-C9heterobicycle compound 2 occurred as expected at position 4.

Sources & evidence

ORD record
ord-eb3c2b9c74cf41e38584ad5bace54e00
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Linked notes

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