Isopropyl iodide → HCID 58174098, compound

HRID 339809Notes

Reaction equation

HRID 339809 reaction equation
[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:21][C:22]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][N:23]=3)=[C:18]([OH:20])[CH:19]=2)=[N:3][CH:2]=1.I[CH:33]([CH3:35])[CH3:34].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH:33]([O:20][C:18]1[CH:19]=[C:14]([CH2:13][CH2:12][NH:11][C:4]2[C:5]3[C:10](=[N:9][CH:8]=[CH:7][N:6]=3)[N:1]=[CH:2][N:3]=2)[CH:15]=[CH:16][C:17]=1[O:21][C:22]1[CH:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=[CH:24][N:23]=1)([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 58174106HCID 58174106, compound

Product 1

HCID 58174098HCID 58174098, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-[2-(pteridin-4-ylamino)-ethyl]-2-(4-trifluoromethylpyridin-2-yloxy)-phenol (200 mg, 0.47 mmol) in 2 mL of DMSO was added 2-iodopropane (62 mg, 0.5 mmol), and K2CO3 (97 mg, 0.7 mmol). The solution was heated 2 h at 50° C., after which TLC analysis indicated absence of starting material. The mixture was poured onto ice. The product precipitated and was collected by suction filtration, washed with H2O, and air dried, yielding {2-[3-(isopropoxy)-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-pteridin-4-ylamine (180 mg; 81% yield) as a light brown solid: ESIMS m/z: 471 ([M+H]+).

Workup

  1. additionThe mixture was poured onto ice
  2. customThe product precipitated
  3. filtrationwas collected by suction filtration
  4. washwashed with H2O, and air
  5. customdried

Sources & evidence

ORD record
ord-2c5e98306cdc46e58a2ff308043d271d
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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