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

HRID 357074Notes

Reaction equation

[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([Cl:21])[NH:10][C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH2:32][Cl:33]>CN(C)C=O>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([Cl:21])[N:10]([CH2:30][CH2:31][CH2:32][Cl:33])[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 78.19 g (250 mmol) of 3-benzyl-6-chloro-5-phenylpyrimidine-2,4(1H,3H)-dione and 55.3 g (400 mmol) of potassium carbonate in 450 ml of N,N-dimethylformamide, 49.4 ml (500 mmol) of 1-bromo-3-chloropropane was added at room temperature. This mixture was stirred at 80° C. for 5 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→2/1) to yield 71.89 g (73.9%, 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→2/1)

Sources & evidence

ORD record: ord-8cbc3eacec5e49abae9e5350591089e8
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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