Isopropanol → 2-Chloro-7-phenylthieno[3,2-d]pyrimidine

HRID 1803911노트

반응식

HRID 1803911 반응식
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:11])[N:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:11][C:8]1[N:9]=[CH:10][C:5]2[S:4][CH:3]=[C:2]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

참가 물질

7

반응물 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 569657247-Bromo-2-chlorothieno(3,2-d)pyrimidine

생성물 1

HCID 582288992-Chloro-7-phenylthieno[3,2-d]pyrimidine수율 141.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 7-bromo-2-chlorothieno[3,2-d]pyrimidine (1.0 g, 4.0 mmol), phenyl boronic acid (0.6 g, 4.9 mmol), Pd[PPh3]4 (0.47 g, 0.4 mmol) and aqueous sodium carbonate (2M, 4.5 mL, 9.0 mmol) in toluene (25 mL)/isopropanol (8 mL) was heated under reflux overnight. The mixture was allowed to cool to room temperature, was diluted with ethyl acetate then washed with 10% aqueous sodium bicarbonate, dried (Na2SO4) filtered and concentrated. The resultant solid was sonicated in diethyl ether (2×70 mL) and the combined ether washes were evaporated to afford the crude product (1.4 g), still containing starting material and OPPh3.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. washthen washed with 10% aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant solid was sonicated in diethyl ether (2×70 mL)
  8. customthe combined ether washes were evaporated

출처 및 근거

ORD 기록
ord-2a30c81c01914e5a8e36d25433f76036
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354408B2

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