Water → 1,3-dibenzyl-5-bromo-6-chloropyrimidine-2,4(1H,3H)-dione

HRID 271423Notes

Reaction equation

[Br:1][C:2]1[C:3](=[O:10])[NH:4][C:5](=O)[NH:6][C:7]=1[Cl:8].[C:11]([O-:14])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:5]([N:6]1[C:7]([Cl:8])=[C:2]([Br:1])[C:3](=[O:10])[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]1=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a stirring solution of 5-bromo-6-chloropyrimidine-2,4(1H,3H)-dione (9.4 g, 41.7 mmol) in DMF (100 mL) at room temperature under argon was added K2CO3 (12.7 g, 91.8 mmol), followed by benzyl bromide (10.5 mL, 88.3 mmol). The reaction mixture was stirred at 75° C. for 1.5 h. After the reaction mixture was cooled to room temperature, water (100 mL) and EtOAc (150 mL) were added. The layers were separated. The organic layer was washed with water (50 mL×2), followed by saturated aqueous NaCl (50 mL), then dried (MgSO4) and concentrated at reduced pressure to obtain crude product. This crude product was passed through a bed of silica gel eluted with CH2Cl2 to obtain 16.5 g of the title compound as a white solid. HPLC/MS: retention time=3.818 min, [M+H]30 =405.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe layers were separated
washThe organic layer was washed with water (50 mL×2)
dry with materialdried (MgSO4)
concentrationconcentrated at reduced pressure
customto obtain crude product
washeluted with CH2Cl2

Sources & evidence

ORD record: ord-333c4ebb3d714d62b7e6062c48d45270
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452892B2

Reaction notes

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