3-{6-[(2,2-Dimethyl-propyl)-methyl-amino]-5-nitro-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide → 3-{5-Amino-6-[(2,2-dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide

HRID 1666079Notes

Reaction equation

HRID 1666079 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[CH2:3][N:4]([CH3:26])[C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:15]([NH:17][CH3:18])=[O:16])[C:6]=1[N+:23]([O-])=O.[H][H]>[Pd]>[NH2:23][C:6]1[C:7]([NH:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:15]([NH:17][CH3:18])=[O:16])=[N:8][CH:9]=[N:10][C:5]=1[N:4]([CH2:3][C:2]([CH3:28])([CH3:27])[CH3:1])[CH3:26]

Participants

4

Reactant 2

HCID 102001653-{6-[(2,2-Dimethyl-propyl)-methyl-amino]-5-nitro-pyrimidin-4-ylamino}-4,N-dimethyl-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 99467743-{5-Amino-6-[(2,2-dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,N-dimethyl-benzamideYield 84.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-{6-[(2,2-Dimethyl-propyl)-methyl-amino]-5-nitro-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide (0.31 g, 0.8 mmol)) was hydrogenated under 40 psi of hydrogen pressure in the presence of 10% Pd/C for 4 hours in Parr instrument. The catalyst was filtered off through celite and the filtrate was concentrated to afford the product (0.24 g, yield 84%). MS (m/z): 357 (M+H).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c572ad1026774538952ea24db22d4c59
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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