4-Fluoroaniline → HCID 86585952, compound

HRID 1634063Notes

Reaction equation

HRID 1634063 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-09b88aac48634f05a38a88d3e0d1226f
Source dataset
uspto-grants-2003_01
Patent number
US06506749B2

Reaction notes

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