Chlorine → HCID 178427972, compound

HRID 1432195Notes

Reaction equation

HRID 1432195 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([OH:11])=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.[Cl:12]Cl>C(O)(=O)C>[Cl:12][C:3]1[S:4][C:5]2[N:6]=[CH:7][N:8]=[C:9]([OH:11])[C:10]=2[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 178431875HCID 178431875, compound

Product 1

HCID 178427972HCID 178427972, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-methylthieno[2,3-d]pyrimidin-4-ol (2 g, 12 mmol) in acetic acid (30 mL) at room temperature, chlorine gas was bubbled for 3 h. The reaction mixture was stirred at same temperature for 2 days. The solvent was evaporated under reduced pressure at 40° C. and the residue was dissolved in ethyl acetate (30 mL) and washed with sat. NaHCO3 solution (3×20 mL). The organic layer was dried over sodium sulfate and evaporated to get the title compound as a pale yellow solid (2 g, 82%). 1H NMR (400 MHz, CDCl3 and CD3OD): δ 7.90 (s, 1H), 2.55 (s, 3H). MS (ESI) m/z: Calculated: 200.65; Observed: 201.3 (M++1).

Workup

  1. customThe solvent was evaporated under reduced pressure at 40° C.
  2. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  3. washwashed with sat. NaHCO3 solution (3×20 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9c2431da5aa841eea6a1a216d6e3800b
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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