(4-Fluoro-2-methylphenyl)boronic acid → HCID 59639640, compound

HRID 556549Notes

Reaction equation

HRID 556549 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([NH:10][CH:11]([CH3:13])[CH3:12])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[C:19]([CH3:26])[CH:18]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:7]([CH:8]=[O:9])=[C:6]([NH:10][CH:11]([CH3:13])[CH3:12])[N:5]=[C:4]([S:14][CH3:15])[N:3]=2)=[C:19]([CH3:26])[CH:18]=1

Participants

3

Reactant 2

HCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 9834732HCID 9834732, compound

Product 1

HCID 59639640HCID 59639640, compound

Procedure

Prepared as described above in Example 11 starting from 4-chloro-6-isopropylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde and 4-fluoro-2-methylphenylboronic acid to give the title compound 4-(4-fluoro-2-methyl-phenyl)-6-isopropylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde. 1H-NMR: δ 1.31 (d, 6H, J=5.7 Hz), 2.21 (s, 3H), 2.59 (s, 3H), 4.52 (m, 1H), 7.90-7.15 (m, 2H), 7.18-7.25 (m, 1H), 9.06 (br s, 1H), 9.50 (s, 1H). LC MS (m/e)=320 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a7ca24a3a170445186733d6d38306db0
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

Loading…