Dichloromethane → HCID 59823054, compound

HRID 2067742Notes

Reaction equation

HRID 2067742 reaction equation
[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]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 6930483(S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolaneHCID 136080886HCID 136080886, compound2×

Product 1

HCID 59823054HCID 59823054, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

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, 4e q) 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.

Workup

  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

Sources & evidence

ORD record
ord-ef9c53ea34da499baad6d6682445520c
Source dataset
uspto-grants-2012_10
Patent number
US08293901B2

Reaction notes

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