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

HRID 1396785노트

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HRID 1396785 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f8aea11eba95427d874f67aefe24f3b8
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901132B2

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