1-Butanol → N-(3-fluorophenyl)-6-iodo-4-pyrimidinamine

HRID 913303Notes

Reaction equation

HRID 913303 reaction equation
I[C:2]1[CH:7]=[C:6]([I:8])[N:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13].C(N(CC)C(C)C)(C)C.C(O)CCC>O>[F:9][C:10]1[CH:11]=[C:12]([NH:13][C:2]2[CH:7]=[C:6]([I:8])[N:5]=[CH:4][N:3]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 97423-FluoroanilineHCID 81531DiisopropylethylamineHCID 157602954,6-Diiodopyrimidine

Product 1

HCID 86646785N-(3-fluorophenyl)-6-iodo-4-pyrimidinamineYield 71.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4,6-diiodopyrimidine (1.0 g, 3.01 mmol), 3-fluoroaniline (290 μL, 3.01 mmol), N,N-diisopropylethylamine (782 μL, 4.52 mmol) and n-butanol (3 mL) under nitrogen was stirred at 120° C. for 4 h. After cooling to room temperature, the solution was poured into water and extracted with ethyl acetate. The organic layer was washed once with 1 N hydrochloric acid, followed by brine, dried and concentrated to yield 0.68 g of title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed once with 1 N hydrochloric acid
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-95c9daeeea0347cba96e69ac48d42b30
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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