Ethanol → 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-one

HRID 634488Notes

Reaction equation

HRID 634488 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([C:22]3[O:23][C:24](=[O:39])[C:25]4[C:30]([C:31]=3[CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:21])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([O:17]C)[CH:14]=[C:13]([F:19])[CH:12]=3)[C:3]=12.C(O)C>C(Cl)Cl.B(Br)(Br)Br>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([C:22]3[O:23][C:24](=[O:39])[C:25]4[C:30]([C:31]=3[CH2:32][N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:21])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:19])[CH:12]=3)[C:3]=12

Participants

5

Reactant 2

HCID 702EthanolHCID 1181314973-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-one

Product 1

HCID 1181313223-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-oneYield 15.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(morpholinomethyl)-1H-isochromen-1-one (0.033 g) in dry DCM (2 ml), 1M BBr3 in DCM (0.93 ml, 0.93 mmol) was added and the solution was stirred at room temperature for 2.5 hrs. The solution was cooled to 0° C. and ethanol (8 ml) was added. The solution was evaporate to dryness and crude was purified by flash chromatography in silica-NH cartridge (DCM to DCM:MeOH=90:10) affording title compound as a pale orange solid (5 mg).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customThe solution was evaporate to dryness and crude
  3. customwas purified by flash chromatography in silica-NH cartridge (DCM to DCM:MeOH=90:10)

Sources & evidence

ORD record
ord-b58d7a26da3d4a6fa294f51a679aa36c
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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