1-Bromo-3-chloropropane → 6-chloro-1-(3-chloropropyl)-3,5-dibenzylpyrimidine-2,4(1H,3H)-dione

HRID 357116Notes

Reaction equation

[Cl:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4](=[O:16])[C:3]=1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][Cl:34]>CN(C)C=O>[Cl:1][C:2]1[N:7]([CH2:31][CH2:32][CH2:33][Cl:34])[C:6](=[O:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4](=[O:16])[C:3]=1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 24.51 g (75 mmol) of 6-chloro-3,5-dibenzylpyrimidine-2,4(1H,3H)-dione and 16.58 g (120 mmol) of potassium carbonate in 120 ml of N,N-dimethylformamide, 14.8 ml (150 mmol) of 1-bromo-3-chloropropane was added at room temperature. This mixture was stirred at 90° C. for 2 hours. After cooling, the reaction mixture was concentrated to dryness; the resulting residue was dissolved in chloroform-water. After the organic layer was washed with water and dried, the solvent was distilled off to yield an oily substance, which was then purified by column chromatography (eluent, n-hexane/ethyl acetate=5/1→3/1) to yield 22.68 g (74.9%, yellow oily substance) of the desired product.

Workup

additionwas added at room temperature
temperatureAfter cooling
concentrationthe reaction mixture was concentrated to dryness
dissolutionthe resulting residue was dissolved in chloroform-water
washAfter the organic layer was washed with water
customdried
distillationthe solvent was distilled off
customto yield an oily substance, which
customwas then purified by column chromatography (eluent, n-hexane/ethyl acetate=5/1→3/1)

Sources & evidence

ORD record: ord-93fa0b5c96694328966cfd43a9eefa0f
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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