Potassium hydroxy sulfite → HCID 53237171, compound

HRID 1966723Notes

Reaction equation

HRID 1966723 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:19])[C:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:30]2[O:34][N:33]=[C:32]([CH3:35])[N:31]=2)=[C:26]([CH:29]=1)[CH:27]=O.OOS([O-])=O.[K+]>CN(C=O)C.O>[C:15]([N:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:19]=[C:27]1[C:26]1[CH:29]=[C:22]([O:21][CH3:20])[CH:23]=[CH:24][C:25]=1[C:30]1[O:34][N:33]=[C:32]([CH3:35])[N:31]=1)([CH3:16])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 58542018HCID 58542018, compound

Product 1

HCID 53237171HCID 53237171, compoundYield 9.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (155 mg, 0.60 mmol) and 5-methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)-benzaldehyde (155 mg, 0.60 mmol) in DMF (10.0 mL) is added Oxone (155 mg, 0.71 mmol) in H2O (2.0 mL). The reaction mixture is stirred at room temperature for 1.5 hours and then quenched with saturated sodium thiosulfate aq. (25 mL). The quenched reaction mixture is extracted with EtOAc (25 mL×2) and the combined organic layers are washed with H2O (50 mL×2), dried with Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 5% MeOH in CH2Cl2 as the eluent to afford the title compound (25 mg, 9%) as a white solid. LCMS (ESMS): m/z 456.20 (M++1)

Workup

  1. customquenched with saturated sodium thiosulfate aq. (25 mL)
  2. customThe quenched reaction mixture
  3. extractionis extracted with EtOAc (25 mL×2)
  4. washthe combined organic layers are washed with H2O (50 mL×2)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customthe residue is purified by silica gel flash column chromatography with 5% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-85cbc210c910439180087885308afc39
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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