Potassium hydroxy sulfite → HCID 58541975, compound

HRID 1966715Notes

Reaction equation

HRID 1966715 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.[CH:20]([C:23]1[N:27]=[C:26]([C:28]2[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=2[CH:30]=O)[O:25][N:24]=1)([CH3:22])[CH3:21].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:30]1[C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[C:26]1[O:25][N:24]=[C:23]([CH:20]([CH3:22])[CH3:21])[N:27]=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 58541981HCID 58541981, compound

Product 1

HCID 58541975HCID 58541975, compoundYield 44%

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 (135 mg, 0.53 mmol) and 2-(3-isopropyl-1,2,4-oxadiazol-5-yl)-benzaldehyde (139 mg, 0.64 mmol) in DMF (5.0 mL) is added Oxone (325 mg, 0.53 mmol) in H2O (2.0 mL). The reaction mixture is stirred at room temperature for 1 hour 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) and dried with Na2SO4. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 3.5% MeOH in CH2Cl2 as the eluent to afford the title compound (105 mg, 44%) as a white solid. LCMS (ESMS): m/z 454.20 (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. concentrationThe filtrate is concentrated under reduced pressure
  7. customthe residue is purified by silica gel flash column chromatography with 3.5% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-95d4ec40bc3341538c0d1a18a2bdc14d
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

Loading…