HCID 11492012, compound → HCID 59258994, compound

HRID 2389989Notes

Reaction equation

HRID 2389989 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:18])[C:5]2[CH:11]=[C:10]([C:12]#[CH:13])[C:9](=[O:14])[N:8]([CH:15]([CH3:17])[CH3:16])[C:6]=2[N:7]=1.[CH2:19]([N:21]([CH2:29][CH3:30])[C:22](=[O:28])[O:23][CH2:24][N:25]=[N+:26]=[N-:27])[CH3:20]>S([O-])([O-])(=O)=O.[Cu+2].CC(O)(C)C.O>[CH2:29]([N:21]([CH2:19][CH3:20])[C:22](=[O:28])[O:23][CH2:24][N:25]1[CH:13]=[C:12]([C:10]2[C:9](=[O:14])[N:8]([CH:15]([CH3:16])[CH3:17])[C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([CH3:18])[C:5]=3[CH:11]=2)[N:27]=[N:26]1)[CH3:30]

Participants

5

Reactant 2

HCID 11492012HCID 11492012, compoundHCID 86619623HCID 86619623, compound

Product 1

HCID 59258994HCID 59258994, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

2-amino-6-ethynyl-8-isopropyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (75 mg, 0.31 mmol) and azidomethyl diethylcarbamate (80 mg, 0.46 mmol) was suspended in 1:1 t-BuOH/H2O (4 mL). To this was added saturated copper sulfate solution (0.05 mL) and stirring was continued for 24 h. The mixture was concentrated and diluted with 5 mL water. The mixture was separated and the organic phase was washed with water and evaporated. Flash chromatography of the residue over silica gel, using 0-5% MeOH/CHCl3, gave the title compound (88 mg, 69%).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 5 mL water
  3. customThe mixture was separated
  4. washthe organic phase was washed with water
  5. customevaporated

Sources & evidence

ORD record
ord-b5f5895d48e6440daecfd592c8bc107e
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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