Sodium Thiosulfate → HCID 53236717, compound

HRID 1966681Notes

Reaction equation

HRID 1966681 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][C:21]1[S:22][CH:23]=[C:24]([C:26]2[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=2[CH:28]=O)[N:25]=1.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:28]1[C:27]1[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=1[C:24]1[N:25]=[C:21]([CH3:20])[S:22][CH:23]=1)([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 585420382-(2-Methyl-thiazol-4-yl)-benzaldehyde

Product 1

HCID 53236717HCID 53236717, compoundYield 84.8%

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 (5 mL) is added 2-(2-methyl-thiazol-4-yl)-benzaldehyde (59 mg, 0.29 mmol) at room temperature. Oxone (119 mg, 0.19 mmol) in H2O (1 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 (10 mL). The combined organic layer is dried (MgSO4), filtered and concentrated and the residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (71 mg, 83%) as a pale brown solid. LCMS (ESMS): m/z 441.20 (M++1)

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL)
  2. dry with materialThe combined organic layer is dried (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-cde1c2c1a98a43af82f72f03feb1ba2c
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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