3-Fluorobenzylic alcohol → 5-Fluoro-4-{2-fluoro-4-[(3-fluorobenzyl)oxy]phenyl}-N-{3-[(methylsulfonyl)methyl]phenyl}pyrimidin-2-amine

HRID 514713Notes

Reaction equation

HRID 514713 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([F:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:18]=2)[N:10]=1.[F:28][C:29]1[CH:30]=[C:31]([CH2:35][OH:36])[CH:32]=[CH:33][CH:34]=1>>[F:15][C:14]1[C:9]([C:3]2[CH:4]=[CH:5][C:6]([O:36][CH2:35][C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([F:28])[CH:30]=3)=[CH:7][C:2]=2[F:1])=[N:10][C:11]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:18]=2)=[N:12][CH:13]=1

Participants

3

Reactant 2

HCID 680083-Fluorobenzylic alcoholHCID 867296154-(2,4-difluorophenyl)-5-fluoro-N-{3-[(methylsulfonyl)methyl]phenyl}pyrimidin-2-amine2×

Product 1

HCID 867296175-Fluoro-4-{2-fluoro-4-[(3-fluorobenzyl)oxy]phenyl}-N-{3-[(methylsulfonyl)methyl]phenyl}pyrimidin-2-amine

Procedure

Example 18 was prepared under similar conditions as described in the preparation of Example 16 using 4-(2,4-difluorophenyl)-5-fluoro-N-{3-[(methylsulfonyl)methyl]phenyl}pyrimidin-2-amine (Intermediate 16.2) and (3-fluorophenyl)methanol (ABCR GmbH & CO. KG). The batch was purified by preparative HPLC.

Workup

  1. customExample 18 was prepared under similar conditions
  2. customThe batch was purified by preparative HPLC

Sources & evidence

ORD record
ord-b6c556e06ded414b9307732a583bb629
Source dataset
uspto-grants-2015_08
Patent number
US09108926B2

Reaction notes

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