Sodium Thiosulfate → HCID 58541937, compound

HRID 1966669Notes

Reaction equation

HRID 1966669 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]([N:30]2[CH:34]=[CH:33][CH:32]=[N:31]2)=[C:26]([CH:29]=1)[CH:27]=O.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>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[N:30]1[CH:34]=[CH:33][CH:32]=[N:31]1)([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 280637435-Methoxy-2-(1H-pyrazol-1-yl)benzaldehydeHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 58541937HCID 58541937, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (50 mg, 0.19 mmol) in DMF (10 mL) is added 5-methoxy-2-(1H-pyrazol-1-yl)benzaldehyde (59 mg, 0.29 mmol) at room temperature. Oxone (119 mg, 0.19 mmol) in H2O (2 mL) is added and the solution is stirred for 1 hour. Saturated sodium thiosulfate solution (5 mL) is added and the mixture is extracted with EtOAc (3×10 mL) and H2O (5 mL). The combined organic layer is dried with MgSO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (56 mg, 67%) as a white solid. LCMS (ESMS): m/z 440.20 (M++1)

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL) and H2O (5 mL)
  2. dry with materialThe combined organic layer is dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel flash column chromatography
  6. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-84b5bd9caf0e44e2b6b867b87fd22a2f
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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