Potassium Carbonate → HCID 66803045, compound

HRID 341480Notes

Reaction equation

HRID 341480 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.Br[CH2:18][CH2:19][O:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH2:18][CH2:19][O:20][CH3:21])[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

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 66803272HCID 66803272, compound

Product 1

HCID 66803045HCID 66803045, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-amino-6-phenylamino-[1,3,5]triazine-2-carbonitrile (prepared in an analogous manner to Intermediate 5, 100 mg, 470 μmol), 1-bromo-2-methoxyethane (50 μl, 0.52 mmol) and potassium carbonate 130 mg, 0.94 mmol) in DMF (5 ml) was heated to 100 C and stirred 3 h. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated under vacuum to give the crude product which was used without further purification (400 mg, >100%, contains DMF). Method C HPLC-MS: MH+ requires m/z=271. Found: m/z=271, Rt=1.23 min (52%).

Workup

  1. temperaturewas heated to 100 C
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-34e07a9b94e348f2826d318afce0658f
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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