Ethyl Acetate → 2-(Methylsulfanyl)pyrimidin-5-ol

HRID 386583

반응식

HRID 386583 반응식
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][N:4]=1.B1([O-])O[O:19]1.O.O.O.O.[Na+].CCOC(C)=O>C1COCC1.O>[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([OH:19])=[CH:5][N:4]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 164142192-(Methylthio)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidineHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

생성물 1

HCID 5883572-(Methylsulfanyl)pyrimidin-5-ol

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a stirring solution of 2-(methylthio)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (from step A) (1.167 g, 4.63 mmol) in THF/H2O (20 mL 1:1) at room temperature under argon was added sodium perborate tetrahydrate (2.137 g, 13.9 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was cooled to room temperature. EtOAc (10 mL) was added to the reaction mixture, which was washed with brine (15 mL×3). Organic phase was dried (MgSO4), filtered and concentrated. The crude product was very insoluble, therefore it was used directly to next step. MS (ESI) 143 (M+H).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. washwas washed with brine (15 mL×3)
  3. dry with materialOrganic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-85b7039681764b56b930fd22abf2fe66
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372837B2

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