Methyl iodide → HCID 66780292, compound

HRID 1958046Notes

Reaction equation

HRID 1958046 reaction equation
[Cl:1][C:2]1[C:3]([CH3:26])=[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=[S:25])[CH:5]=[CH:6][CH:7]=1.[CH3:27]I>O1CCCC1>[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[S:17][C:13]=3[C:12](=[O:24])[N:11]=[C:10]2[S:25][CH3:27])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 70695469HCID 70695469, compound

Product 1

HCID 66780292HCID 66780292, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a vial containing 4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-thioxo-5,6-dihydro[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (25 mg, 0.061 mmol) in Tetrahydrofuran (THF) (607 μl) was added methyl iodide (4.20 μl, 0.067 mmol). The mixture was stirred at room temperature overnight then concentrated. The residue was purified by reversed-phase HPLC to provide 4-[(3-chloro-2-methylphenyl)methyl]-5-(methylthio)-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (6 mg, 23%); LC/MS: MS (ES+) m/e 423 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.44 (s, 3H), 2.47 (s, 3H), 3.52 (m, 4H), 3.63-3.73 (m, 4H), 5.50 (s, 2H), 6.61 (d, J=7.6 Hz, 1H), 7.16 (m, 1H), 7.38 (d, J=7.8 Hz, 1H).

Workup

  1. concentrationthen concentrated
  2. customThe residue was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-e3d11d5998bb44ad8e29a4620935e3d2
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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