3-Carboxyphenylboronic acid → 3-{6-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-benzoic acid

HRID 216119Notes

Reaction equation

HRID 216119 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].Cl[C:14]1[N:19]=[C:18]([S:20][CH3:21])[N:17]=[C:16]([NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=2)[CH:15]=1>>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][NH:22][C:16]2[N:17]=[C:18]([S:20][CH3:21])[N:19]=[C:14]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:1]([OH:3])=[O:2])[CH:15]=2)[CH:30]=[CH:29][C:28]=1[O:31][CH3:32]

Participants

3

Reactant 2

HCID 27339573-Carboxyphenylboronic acidHCID 57636020(6-Chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine

Product 1

HCID 533258483-{6-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-benzoic acid

Procedure

By proceeding in a similar manner to Example 16(a) above but using commercially available 3-carboxy-phenyl-boronic acid, and (6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine (0.57 g) in Step 2, and extracting the reaction mixture (adjusted to pH 2) with EtOAc followed by evaporation of the organic extract, there is prepared 3-{6-[2-(3,4-dimethoxy-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-benzoic acid [0.48 g, Example 16(b)]. LCMS: RT=2.75 minutes, MS: 426 (M+H). IC50=243 nM

Workup

  1. extractionextracting the reaction mixture (adjusted to pH 2) with EtOAc
  2. customfollowed by evaporation of the organic extract, there
  3. customis prepared 3-{6-[2-(3,4-dimethoxy-phenyl)-ethylamino]-2-methylsulfanyl-pyrimidin-4-yl}-benzoic acid [0.48 g, Example 16(b)]

Sources & evidence

ORD record
ord-1b9869732c91495bbb0158a984744e42
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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