Potassium hydroxy sulfite → N4-{2-[(1,1-Dioxido-4-thiomorpholinyl)carbonyl]phenyl}-5-fluoro-N2-{3-[2-(4-morpholinyl)ethyl]phenyl}-2,4-pyrimidinediamine

HRID 1362880Notes

Reaction equation

HRID 1362880 reaction equation
[F:1][C:2]1[C:3]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([N:32]2[CH2:37][CH2:36]S[CH2:34][CH2:33]2)=[O:31])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:10]=2)=[N:6][CH:7]=1.O[O:39][S:40]([O-:42])=O.[K+]>C1COCC1.CO.O>[O:39]=[S:40]1(=[O:42])[CH2:36][CH2:37][N:32]([C:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[NH:23][C:3]2[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[CH:10]=3)[N:4]=2)=[O:31])[CH2:33][CH2:34]1

Participants

6

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 579741995-Fluoro-N2-{3-[2-(4-morpholinyl)ethyl]phenyl}-N4-[2-(4-thiomorpholinylcarbonyl)phenyl]-2,4-pyrimidinediamine

Product 1

HCID 57974146N4-{2-[(1,1-Dioxido-4-thiomorpholinyl)carbonyl]phenyl}-5-fluoro-N2-{3-[2-(4-morpholinyl)ethyl]phenyl}-2,4-pyrimidinediamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-fluoro-N2-{3-[2-(4-morpholinyl)ethyl]phenyl}-N4-[2-(4-thiomorpholinylcarbonyl)phenyl]-2,4-pyrimidinediamine (100 mg, 0.19 mmoles) was dissolved in 5 mL of THF and 5 mL of methanol, and treated with a solution of OXONE® reagent (15 equivalents) in 5 mL water. The system was stirred for 48 h at room temperature, and then filtered and concentrated to dryness. The residue was immobilized onto silica gel and purified by flash chromatography on silica gel, using a gradient of 100% A to 90% A-10% B, where “A” is chloroform and “B” is 10:90:1 methanol-chloroform-concentrated aqueous ammonium hydroxide). The title compound was isolated and characterized. MS: M(C27H31FN6O4S)=554.2, (M+H)+=555.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness
  3. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-bcd1cc55873c48a59f76523f5d94ff9b
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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