Sodium Thiosulfate → HCID 58541938, compound

HRID 1966699Notes

Reaction equation

HRID 1966699 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[CH:25]=[C:24]([CH3:26])[N:23]([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[CH:29]=O)[N:22]=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:29]1[C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[N:23]1[C:24]([CH3:26])=[CH:25][C:21]([CH3:20])=[N:22]1)([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 127467312-(3,5-Dimethyl-1H-pyrazol-1-yl)benzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 58541938HCID 58541938, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (64 mg, 0.25 mmol) in DMF (3 mL) is added 2-(3,5-dimethyl-pyrazol-1-yl)-benzaldehyde (50 mg, 0.25 mmol) at room temperature. Oxone (150 mg, 0.25 mmol) in H2O (1 mL) is added and the solution is stirred at the same temperature for 3 hours. The reaction is poured into water (25 mL) and sodium thiosulfate (sat., 50 mL). The product is extracted into EtOAc (2×) and the combined organics are then dried (MgSO4), filtered, and concentrated. Purification via flash chromatography (4 g silica gel, 0-6% MeOH/CH2Cl2) affords the title compound (50 mg, 46%). LCMS (ESMS): m/z 438.20 (M++1)

Workup

  1. extractionThe product is extracted into EtOAc (2×)
  2. dry with materialthe combined organics are then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography (4 g silica gel, 0-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a5e23221ee9a471ca13623257fe7348f
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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