5-(2-Isopropyl-4-methoxy-5-nitro-phenoxy)-pyrimidine-2,4-diamine → 5-(5-Amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

HRID 925161Notes

Reaction equation

HRID 925161 reaction equation
[CH:1]([C:4]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([N+:21]([O-])=O)=[CH:15][C:5]=1[O:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:21][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:4]([CH:1]([CH3:3])[CH3:2])=[C:5]([CH:15]=1)[O:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 595985755-(2-Isopropyl-4-methoxy-5-nitro-phenoxy)-pyrimidine-2,4-diamine

Product 1

HCID 595985735-(5-Amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 5-(2-isopropyl-4-methoxy-5-nitro-phenoxy)-pyrimidine-2,4-diamine (2.1 g, 6.58 mmol) suspended in ethanol (150 mL) in a Parr bomb, was added 10% palladium on charcoal (210 mg). After hydrogenation in the Parr hydrogenator overnight at 35 psi, the reaction was filtered through celite. The celite pad was washed with ethanol and ethyl acetate and the filtrate was concentrated. Purification with silica gel column chromatography (92/8/0.1 dichloromethane/methanol/ammonium hydroxide) gave 5-(5-amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine as a pale orange solid (468 mg, 25%, (M+H)+=290), which was converted to the hydrochloride salt.

Workup

  1. filtrationAfter hydrogenation in the Parr hydrogenator overnight at 35 psi, the reaction was filtered through celite
  2. washThe celite pad was washed with ethanol and ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. customPurification with silica gel column chromatography (92/8/0.1 dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-77a9163ff4ba40188c22993043e23a11
Source dataset
uspto-grants-2016_03
Patent number
US09284279B2

Reaction notes

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