(4-Fluoro-2-methylphenyl)boronic acid → 4-(2,6-Difluoro-phenylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

HRID 2249991Notes

Reaction equation

HRID 2249991 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([NH:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[F:18])[N:5]=[C:4]([S:19][CH3:20])[N:3]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[C:24]([CH3:31])[CH:23]=1>>[F:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:11]=1[NH:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][C:24]=2[CH3:31])[N:3]=[C:4]([S:19][CH3:20])[N:5]=1

Participants

3

Reactant 2

HCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 99447374-Chloro-6-((2,6-difluorophenyl)amino)-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 102716334-(2,6-Difluoro-phenylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Procedure

Prepared as described above in Example 11 starting from 4-chloro-6-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde and 4-fluoro-2-methyl-phenylboronic acid to give the title compound 4-(2,6-difluoro-phenylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde. 1H-NMR: δ 2.21 (s, 3H), 2.25 (s, 3H), 6.95 (m, 4H), 7.18 (m, 4H), 9.54 (s, 1H), 10.29 (br s, 1H). LC MS (m/e)=390 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7b9ede3b0a194758864392084adc04f5
Source dataset
uspto-grants-2008_01
Patent number
US07314934B2

Reaction notes

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