Potassium Iodide → N-Isopropyl-N-(4-methoxy-phenyl)-2-[2-(pyrimidin-2-ylamino)-phenylamino]-acetamide

HRID 1599079Notes

Reaction equation

HRID 1599079 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][C:8]1[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:24][C:25]([N:27]([CH:36]([CH3:38])[CH3:37])[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)=[O:26]>CN(C=O)C>[CH:36]([N:27]([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=1)[C:25](=[O:26])[CH2:24][NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH3:37])[CH3:38]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 107795342-Bromo-N-isopropyl-N-(4-methoxyphenyl)acetamideHCID 14819594N-Pyrimidin-2-yl-benzene-1,2-diamine

Product 1

HCID 18929587N-Isopropyl-N-(4-methoxy-phenyl)-2-[2-(pyrimidin-2-ylamino)-phenylamino]-acetamideYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-pyrimidin-2-yl-benzene-1,2-diamine (82 mg, 0.441 mmol) in DMF (2 mL) was added potassium carbonate (61 mg, 0.441 mmol), potassium iodide (7 mg, 0.044 mmol), and 2-Bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (126 mg, 0.441 mmol). The resultant reaction mixture was stirred overnight at 60° C. The solvent was removed in vacuo and the crude material partitioned between CH2Cl2 (35 mL) and water (15 mL). The organic phase was separated, dried with MgSO4, filtered and concentrated to a yellow oil which upon trituration with EtOH (6 mL) and filtration gave the title compound (96.7 mg, 0.247 mmol) as yellow crystals: 1H NMR (CDCl3, 300 MHz): 8.36 (d, 2H, J=4.9 Hz), 7.38 (dd, 1H, J=1.2, 7.8 Hz), 7.06-6.90 (m, 6H), 6.75 (t, 1H), 6.66 (t, 1H), 6.36 (dd, 1H, J=1.2, 7.8 Hz), 4.97 (m, 1H), 3.87 (s, 3H), 3.43 (s, 2H), 1.04 (d, 6H, J=6.8 Hz); TLC (EtOAc): Rf =0.62; MS (FAB) m/z 392.0 (MH+).

Workup

  1. customThe resultant reaction mixture
  2. customThe solvent was removed in vacuo
  3. customthe crude material partitioned between CH2Cl2 (35 mL) and water (15 mL)
  4. customThe organic phase was separated
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow oil which upon trituration with EtOH (6 mL) and filtration

Sources & evidence

ORD record
ord-7d09cba5d9024f66b81bb174cc29499e
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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