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

HRID 357130

反応式

HRID 357130 の反応式
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([Cl:15])[NH:10][C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>CN(C)C=O>[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([Cl:15])[N:10]([CH2:24][CH2:25][CH2:26][Cl:27])[C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 9379413-benzyl-6-chloro-1H-pyrimidine-2,4-dione

生成物 1

HCID 150275313-benzyl-6-chloro-1-(3-chloropropyl)pyrimidine-2,4(1H,3H)-dione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 18.93 g (80 mmol) of 3-benzyl-6-chloropyrimidine-2,4(1H,3H)-dione and 17.69 g (128 mmol) of potassium carbonate in 120 ml of N,N-dimethylformamide, 15.8 ml (160 mmol) of 1-bromo-3-chloropropane was added at room temperature. This mixture was stirred at 90° C. for 3 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 13.46 g (53.7%, light yellow powder) of the desired product.

後処理

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

出典と根拠

ORDレコード
ord-6d44e8c1a720436b87fa48b2917bc808
出典データセット
uspto-grants-1998_11
特許番号
US05840732

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