(4-Fluoro-2-methylphenyl)boronic acid → 4-(1-Ethyl-propylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

HRID 2249727Notes

Reaction equation

HRID 2249727 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[N:5]=[C:4]([S:16][CH3:17])[N:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[C:21]([CH3:28])[CH:20]=1>>[CH2:12]([CH:11]([NH:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][C:21]=2[CH3:28])[N:3]=[C:4]([S:16][CH3:17])[N:5]=1)[CH2:14][CH3:15])[CH3:13]

Participants

3

Reactant 2

HCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 98141174-Chloro-6-(1-ethyl-propylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Product 1

HCID 99462394-(1-Ethyl-propylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Procedure

Prepared as described above in Example 11 starting from 4-chloro-6-(1-ethyl-propylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde and 4-fluoro-2-methyl-phenylboronic acid to give the title compound 4-(1-ethyl-propylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde. 1H-NMR: δ 0.92 (m, 6H), 1.54-1.71 (m, 4H), 2.21 (s, 3H), 2.53 (s, 3H), 4.28 (m, 1H), 6.63-7.05 (m, 2), 7.21 (m, 1H), 9.05 (br s, 1H), 10.50 (s, 1H). LC MS (m/e)=348 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2971c5d0b103411c91c4f250d969de2b
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

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