Sodium Thiosulfate → 5-{1-tert-Butyl-2-[2-(5-methyl-1,3,4-thiadiazol-2-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine

HRID 1966694Notes

Reaction equation

HRID 1966694 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:25][C:24]([C:26]2[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=2[CH:28]=O)=[N:23][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:28]1[C:27]1[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=1[C:24]1[S:25][C:21]([CH3:20])=[N:22][N: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 585420582-(5-Methyl-1,3,4-thiadiazol-2-yl)benzaldehyde

Product 1

HCID 585419345-{1-tert-Butyl-2-[2-(5-methyl-1,3,4-thiadiazol-2-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamineYield 13.4%

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, 0.39 mmol) in DMF (3 mL) is added 2-(5-methyl-1,3,4-thiadiazol-2-yl)-benzaldehyde (100 mg, 0.49 mmol) at room temperature. Oxone (240 mg, 0.39 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 (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 impure product which is re-purified via preparative TLC (0.5 mm silica gel, 5% MeOH/CH2Cl2). The product band is isolated to give the title compound (23 mg, 13%). LCMS (ESMS): m/z 442.20 (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)
  6. customgives impure product which
  7. customis re-purified via preparative TLC (0.5 mm silica gel, 5% MeOH/CH2Cl2)
  8. customThe product band is isolated

Sources & evidence

ORD record
ord-644af27c8d594c11ba2dd0e812346289
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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