Triethylamine → HCID 178503431, compound

HRID 1809681Notes

Reaction equation

HRID 1809681 reaction equation
Cl[C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[C:5]2=[CH:4][N:3]=1.[NH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]1.C(N(CC)CC)C>CC(O)C>[C:29]([O:28][C:27](=[O:33])[NH:26][CH:23]1[CH2:22][CH2:21][CH:20]([NH:19][C:2]2[N:7]=[C:6]3[NH:8][N:9]=[C:10]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=4)[C:5]3=[CH:4][N:3]=2)[CH2:25][CH2:24]1)([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 178419079HCID 178419079, compoundHCID 178503430HCID 178503430, compound

Product 1

HCID 178503431HCID 178503431, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 6-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine (from Example 7 supra) (2.5 g, 9.0 mmol) in 2-propanol (100 mL) was added trans-tert-butyl 4-aminocyclohexylcarbamate (2.2 g, 9.9 mmol) followed by triethylamine (1.0 g, 9.9 mmol). The reaction mixture was stirred and heated at reflux for 15 hours. The solvent was then removed under reduced pressure. The residue was extracted with dichloromethane (200 mL) and washed with water (3×25 mL), dried over anhydrous sodium sulfate, filtered and concentrated to afford {4-[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 2.5 g, 61.0%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 15 hours
  3. customThe solvent was then removed under reduced pressure
  4. extractionThe residue was extracted with dichloromethane (200 mL)
  5. washwashed with water (3×25 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-04553879c9b14aaebf944c619dd3f35a
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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