m-Chloroperbenzoic acid → HCID 66780844, compound

HRID 1958044Notes

Reaction equation

HRID 1958044 reaction equation
[Cl:1][C:2]1[C:3]([CH3:27])=[C:4]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[S:17][C:13]=3[C:12](=[O:24])[N:11]=[C:10]2SC)[CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1>ClCCl>[Cl:1][C:2]1[C:3]([CH3:27])=[C:4]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[S:17][C:13]=3[C:12](=[O:24])[NH:11][C:10]2=[O:36])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66780292HCID 66780292, compound

Product 1

HCID 66780844HCID 66780844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[(3-chloro-2-methylphenyl)methyl]-5-(methylthio)-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (25 mg, 0.059 mmol) in Dichloromethane (DCM) (500 μl) was added m-CPBA (13.25 mg, 0.059 mmol) in Dichloromethane (DCM) (300 μl) at 0° C. After stirring at room temperature for 3 h, the solution was washed with 5% aqueous sodium hydrogen sulfite followed by saturated aqueous sodium bicarbonate. The organic layer was dried (sodium sulfate), filtered, and concentrated. The crude was purified by reversed-phase HPLC to provide 4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione. (11 mg, 47%); LC/MS: MS (ES+) m/e 393 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.42 (s, 3H), 3.47-3.54 (m, 4H), 3.63-3.71 (m, 4H), 5.18 (s, 2H), 6.90 (d, J=7.3 Hz, 1H), 7.15 (m, 1H), 7.34 (d, J=7.3 Hz, 1H), 11.37 (s, 1H).

Workup

  1. washthe solution was washed with 5% aqueous sodium hydrogen sulfite
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-3fc82e4d96814b68906e7fbd1a3738e4
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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