Dichloromethane → Methyl 7-(4-fluorophenyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate

HRID 518791ノート

反応式

HRID 518791 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.[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C.ClCCl>O1CCOCC1.Cl[Pd]Cl>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:9]2[C:7]3[N:8]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=3[S:11][C:10]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:27][CH:26]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 2856454-Fluorophenylboronic acidHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86697952HCID 86697952、化合物

生成物 1

HCID 86697960Methyl 7-(4-fluorophenyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate収率 78.4%

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

A mixture of 200 mg of methyl 2-(methylsulfanyl)-7-{[(trifluoromethyl)sulfonyl]oxy}thieno[3,2-d]pyrimidine-6-carboxylate 4 (example 1), 216 mg of 4-fluorophenylboronic acid, 19 mg of dichloropalladium (dppf) and 322 mg of BTPP in 2.5 ml of dioxane under argon is microwave-heated at 120° C. in a sealed tube for 1 h. The medium is taken up with dichloromethane and filtered. The organic phase is washed three times with water, then dried over magnesium sulfate, filtered, and then concentrated under vacuum so as to give a yellow solid. The crude is purified on 80 g of silica, elution being carried out with 0-20% of methanol in dichloromethane, so as to obtain 135 mg of methyl 7-(4-fluorophenyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate in the form of a yellow solid.

後処理

  1. filtrationfiltered
  2. washThe organic phase is washed three times with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum so as
  6. customto give a yellow solid
  7. customThe crude is purified on 80 g of silica, elution

出典と根拠

ORDレコード
ord-6866c4218d694f1fa1f171f7a538c073
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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