Triethylamine → HCID 24828862, compound

HRID 1036314Notes

Reaction equation

HRID 1036314 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.C(N(CC)CC)C.[C:18]([NH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C(O)C>[C:21]([O:20][C:18](=[O:19])[NH:25][CH:26]1[CH2:31][CH2:30][N:29]([C:2]2[N:7]=[CH:6][N:5]=[C:4]3[NH:8][N:9]=[CH:10][C:3]=23)[CH2:28][CH2:27]1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 24828862HCID 24828862, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (J. Amer. Chem. Soc. 1957, 79, 6407-6413) (59 mg, 0.38 mmol) in ethanol (2 ml) was added triethylamine (100 μl, 0.72 mmol) and 4-(N-Boc-amino)piperidine (134 mg, 0.67 mmol). The solution was heated at 80° C. for 3 hours, and then cooled to room temperature. The solution was evaporated to dryness and the residue purified by recrystallisation (isopropanol) to yield the product (32 mg, 26% yield).

Workup

  1. temperaturecooled to room temperature
  2. customThe solution was evaporated to dryness
  3. customthe residue purified by recrystallisation (isopropanol)

Sources & evidence

ORD record
ord-d4519128ee8a40c8b822040f7024951b
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

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