Triethylamine → {4-[3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 1809701Notes

Reaction equation

HRID 1809701 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][C:13](Cl)=[N:14][CH:15]=3)[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:26][C:27]([O:30][C:31]([NH:33][CH:34]1[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36][CH2:35]1)=[O:32])([CH3:29])[CH3:28].CCN(CC)CC>CC(O)C>[C:27]([O:30][C:31](=[O:32])[NH:33][CH:34]1[CH2:35][CH2:36][CH:37]([NH:40][C:13]2[N:12]=[C:11]3[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:9]=[C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=4)[C:16]3=[CH:15][N:14]=2)[CH2:38][CH2:39]1)([CH3:29])([CH3:26])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 86667959HCID 86667959, compound

Product 1

HCID 86667966{4-[3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The mixture of 3-(6-bromo-pyridin-2-yl)-6-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine (from Example 31 supra) (2.65 g, 6.01 mmol), tert-butyl (1r,4r)-4-aminocyclohexylcarbamate (1.53 g, 7.14 mmol) and Et3N (1.4 mL, 9.7 mmol) in IPA (60 mL) was heated at reflux for 16 hours. After cooling to room temperature, the reaction mixture was filtered and solid dried to give {4-[3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester as white powder. (Yield 3.3 g, 89%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationthe reaction mixture was filtered
  4. customsolid dried

Sources & evidence

ORD record
ord-dbaf9e73aea64eada307f9ac529fcaaf
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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