Sodium Thiosulfate → HCID 58542059, compound

HRID 1966696Notes

Reaction equation

HRID 1966696 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.[NH:20]1[CH:24]=[C:23]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)[CH:22]=[N:21]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:27]1[C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[C:23]1[CH:22]=[N:21][NH:20][CH:24]=1)([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 53836832HCID 53836832, compoundHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 58542059HCID 58542059, compoundYield 10.5%

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 (150 mg, 0.58 mmol) in DMF (5 mL) is added 2-(1H-pyrazol-4-yl)-benzaldehyde (100 mg, 0.58 mmol) at room temperature. Oxone (360 mg, 0.58 mmol) in H2O (1 mL) is added and the reaction is stirred at the same temperature for 3 hours. The reaction is poured into water (75 mL) and sodium thiosulfate (sat., 15 mL). The product is extracted into EtOAc (3×) and the combined organics are then dried (MgSO4), filtered, and concentrated. Purification via flash chromatography (12 g silica gel, 0-10% MeOH/CH2Cl2) gives the title compound (25 mg, 10%). LCMS (ESMS): m/z 410.20 (M++1)

Workup

  1. extractionThe product is extracted into EtOAc (3×)
  2. dry with materialthe combined organics are then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography (12 g silica gel, 0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-400a618e09e349f19d4d1265b4290c35
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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