2-Methyl-2-butene → HCID 118131385, compound

HRID 634470Notes

Reaction equation

HRID 634470 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:19]([C:21]3[O:22][C:23](=[O:38])[C:24]4[C:29]([C:30]=3[C:31]3[S:35][C:34]([CH:36]=[O:37])=[CH:33][CH:32]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:18])[CH:12]=3)[C:3]=12.CC(=CC)C.[O-:44]Cl=O.[Na+]>C(O)(C)(C)C.O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:19]([C:21]3[O:22][C:23](=[O:38])[C:24]4[C:29]([C:30]=3[C:31]3[S:35][C:34]([C:36]([OH:44])=[O:37])=[CH:33][CH:32]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:18])[CH:12]=3)[C:3]=12

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 118131460HCID 118131460, compound2×

Product 1

HCID 118131385HCID 118131385, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

5-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehyde (Intermediate F4, 19 mg, 0.036 mmol) was dissolved in 2-methyl-2-butene (300 μl, 2.83 mmol) and t-Butanol (0.5 ml), then a solution of NaClO2 (32.6 mg, 0.360 mmol) and K2H2PO4 (49.0 mg, 0.360 mmol) in 0.5 mL of water added and the mixture stirred at rt for 2 hrs. The reaction was quenched by the addition of 2M HClaqueous (1 ml) and the crude purified via reverse phase chromatography using a Biotage C18 30 g SNAP with a gradient of water and acetonitrile to give the title compound (8 mg, 40.9%) as white solid.

Workup

  1. customThe reaction was quenched by the addition of 2M HClaqueous (1 ml)
  2. customthe crude purified via reverse phase chromatography

Sources & evidence

ORD record
ord-920504c7739b4a499995001321bec5e3
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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