4-Chloro-6-(4-fluorophenyl)pyrimidin-2-amine → N4-[3,5-Difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-6-(4-fluorophenyl)-pyrimidine-2,4-diamine

HRID 16446Notes

Reaction equation

HRID 16446 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[C:6]([F:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[CH:17][C:10]=12.Cl[C:21]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[N:24]=[C:23]([NH2:34])[N:22]=1>>[F:18][C:6]1[CH:5]=[C:4]([NH:19][C:21]2[CH:26]=[C:25]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[N:24]=[C:23]([NH2:34])[N:22]=2)[CH:3]=[C:2]([F:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[CH:17][C:10]=12

Participants

3

Reactant 2

HCID 112183534-Chloro-6-(4-fluorophenyl)pyrimidin-2-amineHCID 179792873,5-difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline

Product 1

HCID 58733331N4-[3,5-Difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-6-(4-fluorophenyl)-pyrimidine-2,4-diamine

Procedure

Analogously to example 25, the title compound is synthesized from 100 mg (0.36 mmol) of [3,5-difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine (from example XXXIV) and 110 mg (0.36 mmol) of 4-chloro-6-(4-fluorophenyl)pyrimidine-2-amine (from example LIX). Purification by preparative HPLC gives the product.

Workup

  1. customPurification by preparative HPLC
  2. customgives the product

Sources & evidence

ORD record
ord-264cf6ce27744ec28c5418ff6d73779a
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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