Potassium Carbonate → HCID 66803180, compound

HRID 341481Notes

Reaction equation

HRID 341481 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]#[N:16])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH:25]1[CH2:27][CH2:26]1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]#[N:16])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 66803272HCID 66803272, compound

Product 1

HCID 66803180HCID 66803180, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-amino-6-phenylamino-[1,3,5]triazine-2-carbonitrile (prepared in an analogous manner to Intermediate 5, 160 mg, 0.75 mmol) in DMF (6 mL) was added potassium carbonate (207 mg, 150 μmol) followed by bromomethyl-cyclopropane (111 mg, 830 μmol). The mixture was heated at 120 C for 3 h, allowed to cool to room temperature before extracting into ethyl acetate (10 mL) and washing with water (3×10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound, which was used without further purification (300 mg, >100%). Method C HPLC-MS: MH+ requires m/z=267. Found: m/z=267, Rt=1.38 min (43%).

Workup

  1. temperatureThe mixture was heated at 120 C for 3 h
  2. extractionbefore extracting into ethyl acetate (10 mL)
  3. washwashing with water (3×10 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2b206194d9147ca881091c4af2ea793
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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