HCID 59643067, compound → HCID 59643093, compound

HRID 2251086Notes

Reaction equation

HRID 2251086 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[C:10]([S:16][CH3:17])[N:9]=2)=[CH:5][C:4]([CH3:18])=[N:3]1>C(Cl)Cl.C1COCC1.[O-2].[Mn+4].[O-2]>[CH3:1][N:2]1[C:6]([NH:7][C:8]2[C:13]([CH:14]=[O:15])=[CH:12][N:11]=[C:10]([S:16][CH3:17])[N:9]=2)=[CH:5][C:4]([CH3:18])=[N:3]1

Participants

4

Reactant 1

HCID 59643067HCID 59643067, compound

Product 1

HCID 59643093HCID 59643093, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of [4-(2,5-dimethyl-2H-pyrazol-3-ylamino)-2-methylsulfanyl-pyrimidin-5-yl]-methanol, 17, (0.97 g, 3.66 mmol) in CH2Cl2/THF (35 mL of 1:1 mixture) is added manganese (IV) oxide (2.54 g, 29.28 mmol). After stirring the suspension at room temperature for 43 hours, the mixture is filtered through celite, and washed with CH2Cl2. The filtrate is concentrated in vacuo and the resulting residue is purified over silica (5% MeOH/chloroform) to afford 0.52 g of the desired product: 1H NMR (300 MHz, CDCl3) δ 8.22 (s, NH), 10.58 (s, NH), 9,86 (s, 1H), 8.54 (s, 1H), 6.36 (s, 1H), 3.81 (s, 3H), 2.58 (s, 3H), 2.30 (s, 3H); ESI+ MS: m/z (rel intensity) 264.0 (100, M++H).

Workup

  1. filtrationthe mixture is filtered through celite
  2. washwashed with CH2Cl2
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe resulting residue is purified over silica (5% MeOH/chloroform)

Sources & evidence

ORD record
ord-cf54be082bec4752a60f77fcc1fa2f42
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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