2,4-Dichloropyrimidine → HCID 86685259, compound

HRID 522926Notes

Reaction equation

HRID 522926 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH2:10][CH2:11][NH2:12])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[Cl:26][C:27]1[N:32]=[C:31](Cl)[CH:30]=[CH:29][N:28]=1>C(O)(C)C>[Cl:26][C:27]1[N:32]=[C:31]([NH:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:13]=[CH:14][C:4]([O:3][C:2]([F:15])([F:16])[F:1])=[CH:5][CH:6]=2)[CH:30]=[CH:29][N:28]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 218322893-[4-(Trifluoromethoxy)phenoxy]propan-1-amine

Product 1

HCID 86685259HCID 86685259, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(4-(trifluoromethoxy)phenoxy)propan-1-amine (450 mg, 1.91 mmol) in isopropanol (8 mL, 3 mL/mmol) was added DIPEA (0.5 mL, 2.86 mmol) and 2,4-dichloropyrimidine (340 mg, 2.29 mmol) and the mixture was stirred at 80° C. for 24 h. Then reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×30 mL) and water (2×30 mL). The EtOAc layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography provided 2-chloro-N-(3-(4-(trifluoromethoxy)phenoxy)propyl)pyrimidin-4-amine (400 mg, 60%) as a solid. Observed mass (M+1): 348.1.

Workup

  1. customThen reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. extractionextracted with EtOAc (2×30 mL) and water (2×30 mL)
  4. washThe EtOAc layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-6c9b2c58778144888f711adca081bc73
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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