Dichloromethane → HCID 59823054、化合物

HRID 1660885ノート

反応式

HRID 1660885 の反応式
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:23][C@@H:24]1[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]1.C(Cl)Cl>CN(C=O)C.[I-].[K+]>[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:23][C@@H:24]3[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]3)[CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[CH3:15]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 6930483(S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolaneHCID 136080886HCID 136080886、化合物2 回

生成物 1

HCID 59823054HCID 59823054、化合物収率 38.4%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

5-Chloro-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (8.3 g, 36.8 mmol, 1 eq, compound 8D), cesium carbonate (47.9 g, 147.5 mmol, 4 eq) and potassium iodide (30 mg, cat) were stirred in anhydrous DMF (180 mL, 0.4 M) containing 4 Å molecular sieves (2.49 g) under N2. After 15 minutes (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (25.1 mL, 184 mmol, 5 eq) was added and the mixture stirred at 120° C. for 12 hours. DCM (150 mL) was added and the organic layer washed with water (150 mL) dried over magnesium sulfate and evaporated. The residue was purified by silica chromatography using 0-70% EtOAc/Hexane as eluent to give 4.8 g of product. [M+H] calc'd for C15H18ClN3O4, 340; found, 340.

後処理

  1. additioncontaining 4 Å molecular sieves (2.49 g) under N2
  2. washthe organic layer washed with water (150 mL)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica chromatography

出典と根拠

ORDレコード
ord-eb4c4af4b6534b7d9267c6a1836ef799
出典データセット
uspto-grants-2011_10
特許番号
US08030317B2

反応ノート

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