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

HRID 16449Notes

Reaction equation

HRID 16449 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=3[F:18])=[C:4]2[CH2:3][CH2:2]1.Cl[C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:23]=[C:22]([NH2:33])[N:21]=1>>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:20]4[CH:25]=[C:24]([C:26]5[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=5)[N:23]=[C:22]([NH2:33])[N:21]=4)=[CH:13][C:12]=3[F:18])=[C:4]2[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 112183534-Chloro-6-(4-fluorophenyl)pyrimidin-2-amineHCID 17979279[4-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl]amine

Product 1

HCID 58733371N4-[4-(2,3-Dihydro-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl]-6-(4-fluoro-phenyl)pyrimidine-2,4-diamine

Procedure

Analogously to example 25, the title compound is synthesized from 35 mg (0.14 mmol) of [4-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluoro-phenyl]amine (from example XLVI) and 39 mg (0.15 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-e0e301745fb346dc99b3011bbbc4d729
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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