2-Nitroaniline → N-(2-Nitro-phenyl)-N'-pyridin-4-ylmethyl-pyrimidine-4,6-diamine

HRID 58166Notes

Reaction equation

HRID 58166 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:3]=1.[N+:16]([C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21])([O-:18])=[O:17].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N+:16]([C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH:21][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[N:5]=[CH:6][N:7]=1)([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 69462-NitroanilineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 467414356-Chloro-N-(4-pyridinylmethyl)-4-pyrimidinamine

Product 1

HCID 118026209N-(2-Nitro-phenyl)-N'-pyridin-4-ylmethyl-pyrimidine-4,6-diamineYield 45.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A degassed mixture of (6-chloro-pyrimidin-4-yl)-pyridin-4-ylmethyl-amine (500 g, 2.27 mmol), 2-nitroaniline (317 g, 2.3 mmol), Pd2(dba)3 (200 g, 0.22 mmol), Xantphos (253 g, 0.44 mmol) and Cs2CO3 (1.48 g, 9.35 mmol) in toluene (10 mL) was heated at 100° C. for 3 hours. The reaction was concentrated, and the residue was purified by reverse phase chromatography followed by flash chromatography on silica to obtain the title compound (330 mg, yield: 45%). MS (ESI): 323 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-6256a2396df5471b87ce602159f413ad
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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