Sodium hydride → 3-(4-chlorobenzyl)-5-bromopyrimidin-4(3H)-one

HRID 2241219Notes

Reaction equation

HRID 2241219 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5](=[O:10])[NH:6][CH:7]=[N:8][CH:9]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1>C1COCC1.CN(C=O)C>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:6]2[C:5](=[O:10])[C:4]([Br:3])=[CH:9][N:8]=[CH:7]2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 882564(3H)-Pyrimidinone, 5-bromo-

Product 1

HCID 663104043-(4-chlorobenzyl)-5-bromopyrimidin-4(3H)-oneYield 15.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.343 g, 8.57 mmol) was added to a solution of 5-bromopyrimidin-4(3H)-one (1.5 g, 8.57 mmol) in THF (10 mL) and DMF (6 mL) and the reaction mixture was stirred for 10 minutes. 4-Chlorobenzyl bromide (1.76 g, 8.57 mmol) was added and the reaction mixture was stirred for an additional 1 hour. The reaction was quenched by pouring the reaction mixture into ice and diluting with ethyl acetate. The organic layer washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (Biotage 40S) to afford the title compound as white solid (0.388 g, 15.1%). LRMS (APCI pos) m/e 300.9 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 8.10 (s, 1H), 7.29-7.37 (m, 4H), 5.15 (s, 2H).

Workup

  1. stirringthe reaction mixture was stirred for an additional 1 hour
  2. customThe reaction was quenched
  3. additionby pouring the reaction mixture into ice
  4. additiondiluting with ethyl acetate
  5. washThe organic layer washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (Biotage 40S)

Sources & evidence

ORD record
ord-042d48adb02440459fa6b7c6933ba2ec
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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