4,6-Dichloropyrimidine → 3-(6-Chloro-pyrimidin-4-ylamino)-4,N-dimethyl-benzamide

HRID 1666086Notes

Reaction equation

HRID 1666086 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:13]([NH:15][CH3:16])=[O:14].CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[CH3:20])[C:13]([NH:15][CH3:16])=[O:14])[CH:7]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 126079733-Amino-N,4-dimethylbenzamide

Product 1

HCID 589285143-(6-Chloro-pyrimidin-4-ylamino)-4,N-dimethyl-benzamideYield 43.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4,6-dichloropyrimidine (2.0 g, 13.4 mmol) in p-dioxane (50 mL), 3-amino-4,N-dimethyl-benzamide (3.0 g, 18.3 mmol) and DIEA (2.3 mL) were added. The resulting mixture was heated to reflux for 4 days. The solvent was removed in vacuo, the residue was taken in water and ethyl acetate, and the ethyl acetate layer was separated and concentrated. The product was purified by silica gel column chromatography using ethyl acetate:hexane (1:1) as eluent to afford the pale white solid product (1.6 g, yield 43%). MS (m/z): 277 (M+H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 days
  3. customThe solvent was removed in vacuo
  4. customethyl acetate, and the ethyl acetate layer was separated
  5. concentrationconcentrated
  6. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-34f8f9f7847f45d8b4cd84fff4351d6c
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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