3,3,3-Trifluoropropylamine → HCID 59354907, compound

HRID 1099459Notes

Reaction equation

HRID 1099459 reaction equation
[H-].[Na+].[F:3][C:4]([F:9])([F:8])[CH2:5][CH2:6][NH2:7].[Br:10][C:11]1[CH:12]=[N:13][C:14](I)=[N:15][CH:16]=1>O1CCCC1>[Br:10][C:11]1[CH:12]=[N:13][C:14]([NH:7][CH2:6][CH2:5][C:4]([F:9])([F:8])[F:3])=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 100013,3,3-TrifluoropropylamineHCID 24758Sodium hydrideHCID 70066515-Bromo-2-iodopyrimidine

Product 1

HCID 59354907HCID 59354907, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (560 mg, 14.0 mmol) was added in portions to a solution of 3,3,3-trifluoro-propylamine (1.59 g, 14.0 mmol) in dry tetrahydrofuran at ambient temperature. The reaction mixture was stirred for 30 min and a solution of 5-bromo-2-iodopyrimidine (2.0 g, 7.0 mmol) in tetrahydrofuran was added. The reaction mixture was stirred for 30 min and then quenched with water (10 mL). The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude residue was purified by column chromatography using a gradient of ethyl acetate in hexane to yield 950 mg (48%) of the title compound; 1H NMR (400 MHz, CDCl3) δ ppm 8.30 (s, 2 H), 5.42 (br. s, 1 H), 3.64 (m, 2 H), 2.41 (m, 2 H).

Workup

  1. stirringThe reaction mixture was stirred for 30 min
  2. customquenched with water (10 mL)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-4b561e6053dd47248e12f75911ad82e4
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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