Triphenylphosphine → tert-butyl 3-((4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carboxylate

HRID 516149Notes

Reaction equation

HRID 516149 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:25]#[C:26][C:27]2[C:35]3[C:30](=[N:31][CH:32]=[N:33][C:34]=3[NH2:36])[NH:29][N:28]=2)[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1.[C:37]([N:44]1[CH2:48][CH2:47][CH:46]([CH2:49]O)[CH2:45]1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:36][C:34]1[N:33]=[CH:32][N:31]=[C:30]2[N:29]([CH2:49][CH:46]3[CH2:47][CH2:48][N:44]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH2:45]3)[N:28]=[C:27]([C:26]#[C:25][C:19]3[CH:18]=[C:17]([O:16][CH3:15])[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=3)[C:35]=12

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 178489940HCID 178489940, compound

Product 1

HCID 89870802tert-butyl 3-((4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (197 μl) was added to a suspension of 3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (148 mg) obtained in Example 1 (Step 1), N-Boc-3-hydroxymethylpyrrolidine (154 mg), polymer supported triphenylphosphine (up to 3.0 mmol/g, 334 mg) in THF (5.0 ml), followed by stirring at room temperature for 3 hours. The insoluble matter was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a colorless, amorphous substance (94.5 mg). Physical properties: m/z [M+H]+ 479.1

Workup

  1. filtrationThe insoluble matter was filtered out
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resulting residue was purified by basic silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2a7e46a768fa4cbd8bd7d7a99f47d6ff
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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