HCID 68165491, compound → HCID 68165223, compound

HRID 921314Notes

Reaction equation

HRID 921314 reaction equation
[CH3:1][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25]([CH:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])[C:15]([N+:31]([O-])=O)=[CH:14][N:13]=2)=[C:7]([O:34][CH3:35])[CH:6]=1)([CH3:4])=[O:3]>C(O)C.[Pd]>[CH3:4][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25]([CH:28]([CH3:29])[CH3:30])(=[O:27])=[O:26])[C:15]([NH2:31])=[CH:14][N:13]=2)=[C:7]([O:34][CH3:35])[CH:6]=1)([CH3:1])=[O:3]

Participants

4

Reactant 1

HCID 68165491HCID 68165491, compound

Product 1

HCID 68165223HCID 68165223, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-5-nitro-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine (461 mg, 0.89 mmol) in Ethanol was added 184 mg of 10% Pd on carbon. The reaction mixture was stirred at room temperature overnight and filtered through celite. The filtrate was concentrated under reduced pressure to yield the crude product. The crude product was purified by silica gel chromatography with 10% Methanol in DCM to yield N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4,5-triamine as a solid. MS ES+: m/z=490.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto yield the crude product
  4. customThe crude product was purified by silica gel chromatography with 10% Methanol in DCM

Sources & evidence

ORD record
ord-0a24e8ad3b664cdfa7db841bf0f5129c
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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