2-Bromoethanol → HCID 67250612, compound

HRID 2421005Notes

Reaction equation

HRID 2421005 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][CH2:11][CH3:12])[C:6]([C:13]2[O:17][C:16](=[O:18])[NH:15][N:14]=2)=[CH:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Br:50][CH2:51][CH2:52]O>O.C1COCC1>[Br:50][CH2:51][CH2:52][N:15]1[N:14]=[C:13]([C:6]2[C:7]([NH:9][CH2:10][CH2:11][CH3:12])=[N:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=2)[O:17][C:16]1=[O:18]

Participants

7

Reactant 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 67249968HCID 67249968, compound

Product 1

HCID 67250612HCID 67250612, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5.0 mL of THF, 5-(2-methylthio-4-propylaminopyrimidin-5-yl)-3H-[1,3,4]oxadiazol-2-one (200 mg) obtained in Step 1 of Example 17 was dissolved, then triphenylphosphine (588 mg), DEAD (40% toluene solution, 1.02 mL, 2.34 mmol) and 2-bromoethanol (280 mg) were added thereto, followed by stirring at room temperature for 1 hour. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was added with water and was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to give 3-bromoethyl-5-(2-methylthio-4-propylaminopyrimidin-5-yl)-3H-[1,3,4]oxadiazol-2-one [Compound (P) in which R1 represents n-propylamino, R8A represents 2-bromoethyl] (210 mg, yield 75%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-a6d68eb1f35643f5ac49cc56a6ad1af7
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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