3-Chloroaniline → HCID 67389780, compound

HRID 913282Notes

Reaction equation

HRID 913282 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10](Cl)[N:9]=2)[N:5]=[CH:4][N:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].[NH2:23][CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>O1CCCC1>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]([NH:23][CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[N:9]=3)[N:5]=[CH:4][N:3]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 4192234-AminotetrahydropyranHCID 86646773HCID 86646773, compound2×

Product 1

HCID 67389780HCID 67389780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-4-(2-chloro-4-pyrimidinyl)-1,3,5-triazine (i.e., the product of Example 1, Step B) (25 mg, 0.11 mmol) in tetrahydrofuran (1.0 mL) was added 3-chloroaniline (0.1 mL), and the resulting mixture was stirred at room temperature for 3 h to provide a yellow suspension. To this suspension added 4-aminotetrahydropyran (0.2 mL), and the mixture was refluxed for 5 h. The solution was concentrated and purified using column chromatography on silica gel eluted with 70% ethyl acetate in hexanes to give 25 mg of the title compound as a yellow solid.

Workup

  1. customto provide a yellow suspension
  2. temperaturethe mixture was refluxed for 5 h
  3. concentrationThe solution was concentrated
  4. custompurified
  5. washeluted with 70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d5e8e17be536479b8ae7b4044903d87f
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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