Dichloromethane → 2-((4-amino-3-(3-hydroxypropyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one

HRID 1476206Notes

Reaction equation

HRID 1476206 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:15][C:16]3[O:17][C:18]4[C:23]([C:24](=[O:32])[C:25]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:9]=[C:10]([C:11]#[C:12][CH2:13][OH:14])[C:3]=12.ClCCl>CO.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:15][C:16]3[O:17][C:18]4[C:23]([C:24](=[O:32])[C:25]=3[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:9]=[C:10]([CH2:11][CH2:12][CH2:13][OH:14])[C:3]=12

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 582691602-((4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one

Product 1

HCID 582691562-((4-amino-3-(3-hydroxypropyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-oneYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of example 59 (0.170 g, 0.401 mmoles) in methanol (4 ml), palladium on charcoal 1 (10%, 0.050 g) was added and hydrogenated at 5 kg/cm2 for 48 h. The reaction mixture filtered through celite pad and washed with methanol. The filtrate was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as brown solid (0.072 g, 42% yield). MP: 182-184° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.11(s,1H), 8.05(dd, J=8.0, 1.6Hz, 1H), 7.76(m,1H), 7.49(t, J=7.1Hz, 1H), 7.39-7.20(m, 8H), 4.62(t, J=4.6Hz, 1H),3.45(q, J=6.1Hz, 2H), 2.92(t, J=7.4Hz, 2H), 1.78(m,2H). Mass: 427.87(M+).

Workup

  1. filtrationThe reaction mixture filtered through celite pad
  2. washwashed with methanol
  3. dry with materialThe filtrate was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-f2ac55f0ef204e4ca0d09968d7f6aced
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

Loading…