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

HRID 386583

Reaction equation

HRID 386583 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 5883572-(Methylsulfanyl)pyrimidin-5-ol

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-85b7039681764b56b930fd22abf2fe66
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Linked notes

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