Potassium Carbonate → 2,5-dichloro-N-(3-iodo-4-methoxyphenyl)pyrimidin-4-amine

HRID 541905

Reaction equation

HRID 541905 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:11][C:12]1[N:17]=[C:16]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:2]([I:1])[CH:3]=2)[C:15]([Cl:19])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 220545963-Iodo-4-methoxyaniline

Product 1

HCID 579618942,5-dichloro-N-(3-iodo-4-methoxyphenyl)pyrimidin-4-amineYield 120.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-iodo-4-methoxyaniline (8.0 g, 0.021 mol) and 2,4,5-trichloropyrimidine (4.13 g, 0.0225 mol) in N,N-dimethylformamide (57 mL) was added potassium carbonate (7.40 g, 0.0536 mol). The resultant mixture was stirred overnight at room temperature. The reaction mixture was filtered to remove K2CO3 and concentrated to give the residue (10 grams). The residue was triturated with EtOAc, and filtered under vacuum. The residue was purified by silica gel column chromatography to give the desired product (2.54 g, 30%). LCMS for C11H9Cl21N3O (M+H)+: m/z=396.0, 398.0.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove K2CO3
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0e0f0b6938264464b5917390d75944aa
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Linked notes

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