1-[(2,3-Dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]-2-methylpropan-2-ol → 1-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]-2-methylpropan-2-ol

HRID 352007

Reaction equation

HRID 352007 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([NH:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])[C:5]([N+:15]([O-])=O)=[C:4]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1>[Pt].C1(C)C=CC=CC=1.C(O)(C)C>[NH2:15][C:5]1[C:4]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:3][C:2]([CH3:1])=[C:7]([CH3:8])[C:6]=1[NH:9][CH2:10][C:11]([CH3:12])([OH:13])[CH3:14]

Participants

4

Reactant 1

HCID 129912011-[(2,3-Dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]-2-methylpropan-2-ol

Product 1

HCID 129912021-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]-2-methylpropan-2-ol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21881414Toluene isopropyl alcoholSolvent

Procedure

To a 500 ml Parr hydrogenation flask was added 5% platinum on carbon (1.432 g) and a solution of 1-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]-2-methylpropan-2-ol in 90/10 toluene/isopropanol (105 ml). The flask was evacuated until the solvent bubbled, and hydrogen was pressured into the flask at 207 kPa. After three evacuation cycles the flask was pressurized with hydrogen to 345 kPa and mixed on a shaker for about 2 hours. The pressure was released, and thin layer chromatography (TLC) monitoring of the reaction mixture indicated complete reaction. The reaction mixture was filtered, and the solvent was removed under reduced pressure. The resulting product was used in the next step.

Workup

  1. customThe flask was evacuated until the solvent
  2. custombubbled
  3. additionmixed on a shaker for about 2 hours
  4. customreaction
  5. filtrationThe reaction mixture was filtered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-44459ba6d2e4470ea54e583d2f7d30cb
Source dataset
uspto-grants-2004_06
Patent number
US06743920B2

Linked notes

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