2-Methoxyaniline → HCID 4542663, compound

HRID 2091974Notes

Reaction equation

HRID 2091974 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[O:10]([C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14])[CH3:11].O1CCOCC1>C(#N)C.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:10][CH3:11])[C:5]([F:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 312751,4-DioxaneHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 4542663HCID 4542663, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
85 °C

Procedure

A round-bottomed flask was charged with 2,4-dichloro-5-fluoropyrimidine (0.84 g, 5 mmol), 2-methoxylaniline (0.61 g, 5 mmol) and dioxane (5 mL). The reaction mixture was heated at 85° C. overnight. The reaction was cooled down and diluted with acetonitrile/water, stirred for 30 min. and filtered. The collected solid was re-suspended in acetonitrile/water, stirred and filtered to give a 2-chloro-5-fluoro-N-(2-methoxyphenyl)pyrimidin-4-amine (0.9 g, 70% yield). To a seal tube was added 2-chloro-5-fluoro-N-(2-methoxyphenyl)pyrimidin-4-amine (254 mg), 3-methoxyaniline (500 mg, 4 eq.) and dioxane (5 mL). The mixture was heated to 130° C. overnight. The reaction mixture was cooled and partitioned between EtOAc and water. The organic layer was concentrated; the residue was triturated with a 1:1 mixture of dichloromethane and acetonitrile, then filtered to give the title product as a white solid (150 mg).

Workup

  1. temperatureThe reaction was cooled down
  2. filtrationfiltered
  3. stirringstirred
  4. filtrationfiltered

Sources & evidence

ORD record
ord-2188b0cf767a463a9793d44be56e054c
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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