Benzyl Bromide → HCID 58879150, compound

HRID 1365736Notes

Reaction equation

HRID 1365736 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][CH2:6][C:7]1[NH:8][C:9](=[O:19])[C:10]([OH:18])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.CCOCC>[CH2:26]([O:18][C:10]1[C:9](=[O:19])[N:8]2[C:7]([CH2:6][S:5][CH2:4][CH2:3][CH2:2]2)=[N:12][C:11]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 136094120HCID 136094120, compound

Product 1

HCID 58879150HCID 58879150, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 2-((3-chloropropylthio)methyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (5 g, 16 mmol) and K2CO3 (4.5 g, 32.5 mmol) in DMF (150 mL) was placed in preheated oil bath and stirred for 1.5 h. After this, benzylbromide (2.4 mL, 20 mmol) was added and continued stirring for additional 3 h. Then, the reaction mixture was cooled, diluted with ether (250 mL0, washed with water (3×50 mL). The combine aq. layers extracted with ether (4×100 mL) and combined with previous organic phase, and washed with brine (50 mL). The organic layer was dried (Na2SO4/activated carbon), filtered and concentrated to give viscous paste. Crystalization of this paste from CH2Cl2/hexanes provided the product as a white solid (4.4 g, 75%). 1H NMR (500 MHz, CDCl3) δ: 7.48-7.46 (2H, m), 7.37-7.30 (3H, m), 5.25 (2H, s), 4.36-4.31 (4H, m), 3.89 (2H, s), 2.94 (2H, t, J=5.6 Hz), 2.16-2.12 (2H, m), 1.30 (3H, t, J=7.0 Hz). HRMS (M+H) calcd for C18H21N2O4S: 361.1222; found: 361.1221.

Workup

  1. customwas placed in preheated oil bath
  2. stirringcontinued stirring for additional 3 h
  3. temperatureThen, the reaction mixture was cooled
  4. washwashed with water (3×50 mL)
  5. extractionThe combine aq. layers extracted with ether (4×100 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialThe organic layer was dried (Na2SO4/activated carbon)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give viscous paste
  11. customCrystalization of this paste from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-2224e43da8ca4c00b619d2f41aea482e
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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