4-Fluoroaniline → HCID 86585952, compound

HRID 982615Notes

Reaction equation

HRID 982615 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C(#N)C>[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 86585952HCID 86585952, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (Aldrich, 24 g, 103 mmol) in 250 mL of acetonitrile at room temperature was added 4-fluoroaniline (22.75 g, 205 mmol). After stirring for two days, the mixture was heated at 60° C. for four hours. The resulting solid was filtered and washed with EtOAc. The filtrate was concentrated, diluted in EtOAc (300 L), washed with brine, dried (MgSO4), filtered and concentrated to provide a crude product. The crude product was stirred with hexanes (400 mL) and then filtered to give 23 g of the ethyl 4-(4-fluorophenyl)amino-2-methylthiopyrimidine-5-carboxylate as a white solid.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. additiondiluted in EtOAc (300 L)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto provide a crude product
  10. filtrationfiltered

Sources & evidence

ORD record
ord-3e22a24025ce4c3c8bf4635c8f28d643
Source dataset
uspto-grants-2005_03
Patent number
US06861423B2

Reaction notes

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