Sodium;3-oxidodioxaborirane;tetrahydrate → HCID 66779850, compound

HRID 1958043Notes

Reaction equation

HRID 1958043 reaction equation
[Cl:1][C:2]1[C:3]([CH3:33])=[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]2[CH2:25][S:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:5]=[CH:6][CH:7]=1.B1([O-])OO1.[OH2:38].[OH2:39].O.O.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([CH3:33])=[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]2[CH2:25][S:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:39])=[O:38])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 66780119HCID 66780119, compound

Product 1

HCID 66779850HCID 66779850, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-[(phenylthio)methyl][1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (37 mg, 0.074 mmol) in Acetic Acid (371 Ml) was added to a stirred suspension of sodiumperborate tetrahydrate (45.6 mg, 0.297 mmol) and Acetic Acid (371 μl). The mixture was stirred at room temperature overnight, and then concentrated. The residue was taken up in dichloromethane/water and eluted through a hydromatrix cartridge. The eluate was concentrated and purified by reversed-phase HPLC to provide 4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-[(phenylsulfonyl)methyl][1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (8 mg, 20%); LC/MS: MS (ES+) m/e 531 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.42 (s, 3H), 3.49-3.55 (m, 4H), 3.64-3.71 (m, 4H), 4.82 (s, 2H), 5.64 (s, 2H), 6.43 (d, J=7.6 Hz, 1H), 7.13 (m, 1H), 7.39 (d, J=7.83 Hz, 1H), 7.65 (t, J=7.8 Hz, 2H), 7.75-7.83 (m, 1H), 7.84-7.90 (m, 2H).

Workup

  1. concentrationconcentrated
  2. washeluted through a hydromatrix cartridge
  3. concentrationThe eluate was concentrated
  4. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-5be7fb6e325546d39a3a3820ec266904
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

Loading…