2,4-Dimethoxyaniline → HCID 79081633, compound

HRID 2117649Notes

Reaction equation

HRID 2117649 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([F:20])=[CH:15][N:14]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:12][C:13]1[N:18]=[C:17]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:3]=2[O:2][CH3:1])[C:16]([F:20])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 176522,4-DimethoxyanilineHCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 79081633HCID 79081633, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,4-dimethoxyaniline (4.1 g, 24.6 mmol) was added to a solution of 2,4-dichloro-5-fluoropyrimidine (4.1 g, 24.6 mmol) in isopropanol (16 mL). N,N-Diisopropyl-ethylamine (6.30 g, 8.50 mL, 48.8 mmol) was added and the mixture was allowed to stir at room temperature for 24 h. The solution was partitioned between ethyl acetate and water. The organic phase was separated and washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford an oil. This oil was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-methylenechloride) to afford (2-chloro-5-fluoro-pyrimidin-4-yl)-(2,4-dimethoxy-phenyl) amine. MS (MH+) 284; Calculated 283.69 for C12H11ClFN3O2.

Workup

  1. customThe solution was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford an oil
  8. customThis oil was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-methylenechloride)

Sources & evidence

ORD record
ord-ff7c57b8d0ea413e9deeeeb9f26f3bc1
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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