Sodium Thiosulfate → HCID 53239643, compound

HRID 1966702Notes

Reaction equation

HRID 1966702 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][C:32]([CH3:35])=[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][C:32]([CH3:35])=[N:31]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 58542000HCID 58542000, compound

Product 1

HCID 53239643HCID 53239643, compoundYield 38%

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 (100 mg, 0.38 mmol) in DMF (3 mL) is added 5-methoxy-2-(3-methyl-pyrazol-1-yl)-benzaldehyde (90 mg, 0.42 mmol) at room temperature. Oxone (230 mg, 0.38 mmol) in H2O (1 mL) is added and the solution is stirred at the same temperature for 12 hours. The reaction is poured into water (25 mL) and sodium thiosulfate (sat., 20 mL). The product is extracted into EtOAc (3×) and the combined organics are then dried (MgSO4), filtered, and concentrated. Purification via flash chromatography (silica gel, 0-8% MeOH/CH2Cl2) affords the title compound (65 mg, 38%). LCMS (ESMS): m/z 454.20 (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 (silica gel, 0-8% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a7874d362ddb49e7a099cf84ccea76d7
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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