2-Fluorophenylboronic acid → 4-Sec-butylamino-6-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

HRID 556548Notes

Reaction equation

HRID 556548 reaction equation
[CH:1]([NH:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10](Cl)[N:9]=[C:8]([S:15][CH3:16])[N:7]=1)([CH2:3][CH3:4])[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O>>[CH:1]([NH:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[F:17])[N:9]=[C:8]([S:15][CH3:16])[N:7]=1)([CH2:3][CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 27343542-Fluorophenylboronic acidHCID 596395844-Sec-butylamino-6-chloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Product 1

HCID 596395354-Sec-butylamino-6-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Procedure

Prepared as described above in Example 11 starting from 4-sec-butylamino-6-chloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde and 2-fluorophenylboronic acid to give the title compound 4-sec-butylamino-6-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde. 1H-NMR: δ 0.96 (m, 3H), 1.30 (m, 3H), 1.67 (m, 2H), 2.58 (s, 3H), 4.38 (m, 1H), 7.11-7.31 (m, 2H), 7.42-7.58 (m, 2H), 9.07 (br s, 1H), 9.63 (s, 1H). LC MS (m/e)=306 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1ae60e2b4b334b97917ed85682165315
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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