Triphenylphosphine → HCID 54675631, compound

HRID 2175385Notes

Reaction equation

HRID 2175385 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:11]3[S:18][C:17]([C:19]4[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=4)=[CH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1.[OH:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:11]3[S:18][C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[CH:21][CH:20]=4)=[CH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5363146Diisopropyl azodicarboxylateHCID 86678556HCID 86678556, compound

Product 1

HCID 54675631HCID 54675631, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-methoxyphenyl)-6-(4-bromophenyl)thieno[3,2-d]pyrimidine-4-amine (0.26 g, 0.76 mmol) was dissolved in 5 ml of degassed dimethylformamide and added with 4-(2-hydroxyethyl)morpholine (0.12 ml, 0.92 mmol) and triphenylphosphine (241 mg, 0.92 mmol). The mixture was further added with DIAD (0.18 ml, 0.92 mmol) at 0° C. and stirred at room temperature for 15 hours. It was extracted with 50 ml saturated sodium bicarbonate and 50 ml of ethylacetate and the organic layer was washed with 50 ml of water twice, dried with magnesium sulfate and filtered. After concentration under vacuum, column chromatography (dichloromethane/methanol, 15/1) was done. The title compound (100 mg, 29%) was obtained as ivory colored solid.

Workup

  1. extractionIt was extracted with 50 ml saturated sodium bicarbonate and 50 ml of ethylacetate
  2. washthe organic layer was washed with 50 ml of water twice
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationAfter concentration under vacuum, column chromatography (dichloromethane/methanol, 15/1)

Sources & evidence

ORD record
ord-5b40c54851d949cfad5d214bc17ef283
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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