1-Bromo-2-nitrobenzene → 2-(2-Pyrimidinyl)benzenamine

HRID 1816286Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Br)([O-])=O.Br[C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1>>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

Reactant 2

HCID 113411-Bromo-2-nitrobenzene

HCID 783452-Bromopyrimidine

Product 1

HCID 224932552-(2-Pyrimidinyl)benzenamine

Procedure

2-Nitrobromobenzene (2.02 g) and 2-bromopyrimidine (0.80 g) were coupled as in Example 83, and the product reduced as in Example 64 to give 2-(2-aminophenyl)pyrimidine. This was reacted with CMI under conditions described in the general procedure for CMI couplings to give N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-(2-pyrimidinyl)aniline.

Sources & evidence

ORD record: ord-cf6c915a804142bd988b20796bc9e39a
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884801B1

Reaction notes

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