3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-[6-(2-nitro-phenylamino)pyrimidin-4-yl]1-pyridin-3-ylmethyl-urea → 1-[6-(2-Amino-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-pyridin-3-ylmethyl-urea

HRID 58132Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH:13][C:14](=[O:39])[N:15]([C:23]1[CH:28]=[C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N+:36]([O-])=O)[N:26]=[CH:25][N:24]=1)[CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1>CC(O)=O.[Fe]>[NH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][C:27]1[N:26]=[CH:25][N:24]=[C:23]([N:15]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:14]([NH:13][C:3]2[C:2]([Cl:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=2[Cl:12])=[O:39])[CH:28]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-[6-(2-nitro-phenylamino)-pyrimidin-4-yl]-1-pyridin-3-ylmethyl-urea (85 g, 0.149 mmol) and Fe (84 g, 1.5 mmol) in AcOH (5 mL) was heated at 50° C. for 2 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give crude product, which was purified by silica gel column chromatography to afford the title compound (53 mg, yield: 66%). MS (ESI): 540 [M+H]+.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customto give crude product, which
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c197e5073e5441919dd53cab972b80f6
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434697B2

Reaction notes

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