Dimethyl Sulfoxide → HCID 178503375, compound

HRID 928234Notes

Reaction equation

HRID 928234 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]2[NH:9][N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]2=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.Br[CH2:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:32][CH2:31]1>C1COCC1.O>[CH3:1][S:2][C:3]1[N:8]=[C:7]2[N:9]([CH2:29][C@H:30]3[CH2:31][CH2:32][C@H:33]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:34][CH2:35]3)[N:10]=[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]2=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 178453876HCID 178453876, compoundHCID 1785033766-(Methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178503375HCID 178503375, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

A microwave tube was charged with 6-(methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine (0.073 g, 0.30 mmol), potassium carbonate (0.14 g, 0.90 mmol), and DMSO (1 mL). The resulting mixture was stirred for 20 min, then was added a solution of tert-butyl trans-4-(bromomethyl)cyclohexylcarbamate (0.10 g, 0.36 mmol) in THF (2 mL). The resulting mixture was heated at 150° C. for 10 min in microwave. The reaction mixture was poured into water and extracted with Et2O (3×). The combined ether layer was dried (Na2SO4) and concentrated. The crude mixture was purified by Isco to provide tert-butyl trans-4-((6-(methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate (0.12 g, 88%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.11 (s, 1H), 7.90 (d, J=7.2 Hz, 2H), 7.55-7.44 (t, J=6.8 Hz, 2H), 7.41 (t, J=7.3 Hz, 1H), 4.37 (bs, 1H), 4.27 (d, J=7.1 Hz, 2H), 3.37 (bs, 1H), 2.61 (s, 3H), 2.09-1.89 (m, 3H), 1.67 (d, J=12.1 Hz, 2H), 1.39 (s, 9H), 1.19 (dd, J=24.4, 10.8 Hz, 2H), 1.04 (ddd, J=25.4, 12.7, 2.9 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 170.1, 155.3, 154.8, 152.3, 144.3, 132.2, 129.2, 127.1, 109.3, 79.3, 52.5, 49.7, 37.7, 32.9, 29.6, 28.5, 12.5; MS m/z 454.2 [M+H]+.

Workup

  1. extractionextracted with Et2O (3×)
  2. dry with materialThe combined ether layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude mixture was purified by Isco

Sources & evidence

ORD record
ord-aaed6c62b6d4402bb376c5f54491458d
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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