Dichloromethane → HCID 59823054, 화합물

HRID 1660885노트

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HRID 1660885 반응식
[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]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 6930483(S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolaneHCID 136080886HCID 136080886, 화합물2회

생성물 1

HCID 59823054HCID 59823054, 화합물수율 38.4%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eb4c4af4b6534b7d9267c6a1836ef799
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030317B2

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