m-Chloroperbenzoic acid → 4-(2-Fluoro-4-nitrophenoxy)-6-(methylsulfinyl)thieno[3,2-d]pyrimidine

HRID 500906Notes

Reaction equation

HRID 500906 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:6]2[S:13][C:12]([S:14][CH3:15])=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1.C1C=C(Cl)C=C(C(OO)=[O:31])C=1>C(Cl)Cl>[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:6]2[S:13][C:12]([S:14]([CH3:15])=[O:31])=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 594244784-(2-Fluoro-4-nitrophenoxy)-6-(methylthio)thieno[3,2-d]pyrimidine

Product 1

HCID 594245544-(2-Fluoro-4-nitrophenoxy)-6-(methylsulfinyl)thieno[3,2-d]pyrimidineYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 281 (1.1 g, 3.2 mmol) and m-CPBA (77%, 890 mg, 12.8 mmol) in DCM at 0° C. was stirred for 2 hours, diluted with DCM, washed with ice water, NaHCO3 solution and water again; dried and concentrated to give the title compound 284 (1.15 g, quantitative) as a yellowish solid. MS (m/z): 354.0(M+H) (found).

Workup

  1. washwashed with ice water, NaHCO3 solution and water again
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fd698de052aa4239b0f4cd480f720472
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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