Phenylboronic Acid → Methyl 2-(methylthio)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate

HRID 518783ノート

反応式

HRID 518783 の反応式
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9](OS(C(F)(F)F)(=O)=O)[C:7]=2[N:8]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C>Cl[Pd]Cl.O1CCOCC1>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:7]=2[N:8]=1

参加物

6

反応物 3

HCID 66827Phenylboronic AcidHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86697952HCID 86697952、化合物

生成物 1

HCID 86697951Methyl 2-(methylthio)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate収率 78.6%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 312751,4-Dioxane溶媒

実験手順

Anhydrous dioxane is added, under argon, to a mixture of 2.5 g of methyl 2-(methylsulfanyl)-7-{[(trifluoromethyl)sulfonyl]oxy}thieno[3,2-d]pyrimidine-6-carboxylate 4 (example 1) and 0.785 g of phenylboronic acid. After the addition of 250 mg of dichloropalladium (dppf) and 4.09 g of BTPP, the mixture is refluxed for 20 h, and then cooled to ambient temperature. The mixture is filtered on silica gel, elution being carried out with ethyl acetate. The solvent is evaporated off under vacuum and the residue is triturated with an ethyl acetate/heptane mixture so as to obtain 1.6 g of methyl 2-(methylsulfanyl)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate in the form of a whitish precipitate.

後処理

  1. temperaturethe mixture is refluxed for 20 h
  2. filtrationThe mixture is filtered on silica gel, elution
  3. customThe solvent is evaporated off under vacuum
  4. customthe residue is triturated with an ethyl acetate/heptane mixture so as

出典と根拠

ORDレコード
ord-1ab7a8cf87c04e34a5341b129eba1404
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

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