Hydrochloric Acid → 4-Chloro-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine

HRID 1507865ノート

反応式

HRID 1507865 の反応式
Br[C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([Cl:10])[C:4]=2[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].Cl>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:10][C:9]1[C:4]2[CH:3]=[C:2]([C:16]3[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=3)[S:11][C:5]=2[N:6]=[CH:7][N:8]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 122252616-Bromo-4-chlorothieno[2,3-d]pyrimidine

生成物 1

HCID 866624414-Chloro-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine収率 47.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

A solution of 6-bromo-4-chlorothieno[2,3-d]pyrimidine (0.12 g, 0.48 mmol), 4-fluorophenylboronic acid (67 mg, 0.48 mmol), K2CO3 (0.266 g, 1.92 mmol) and Pd(PPh3)4 in dioxane/H2O (3:1, 3 ml) was refluxed under N2 for 2 hours. After cooling to room temperature, 1N HCl was added slowly to neutralize the mixture to pH=7-8. The mixture was extracted with CH2Cl2, washed with water and brine and dried over Na2SO4. After removing the solvents under reduced pressure, the crude residue was purified by silica gel chromatography (hexane/EtOAc 30:1) to yield the title compound as a pale yellow solid (60 mg, 47%).

後処理

  1. extractionThe mixture was extracted with CH2Cl2
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvents under reduced pressure
  5. customthe crude residue was purified by silica gel chromatography (hexane/EtOAc 30:1)

出典と根拠

ORDレコード
ord-38d9360e23cb4396aabd481d0b949c92
出典データセット
uspto-grants-2015_12
特許番号
US09221822B2

反応ノート

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