Triethylamine → HCID 178512736, compound

HRID 570541Notes

Reaction equation

HRID 570541 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[N:12][CH:13]=[C:8]2[C:7]([C:14](=[NH:16])[NH2:15])=[N:6]1.C([N:23](CC)CC)C.O.NN>C(O)C>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[N:12][CH:13]=[C:8]2[C:7]([C:14](=[NH:15])[NH:16][NH2:23])=[N:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 866921071-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide

Product 1

HCID 178512736HCID 178512736, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

610 mg (approx. 1.92 mmol, purity 86%) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide were initially charged in 10 ml of ethanol and cooled to 0° C. 777 mg (7.68 mmol) of triethylamine and 120 mg (1.920 mmol) of 80% hydrazine hydrate were added, and the mixture was stirred at room temperature for 18 h. The mixture was concentrated on a rotary evaporator, taken up in ethyl acetate and washed three times with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, concentrated on a rotary evaporator and dried under high vacuum. 590 mg (purity 89%, 95% of theory) of the target compound were obtained.

Workup

  1. concentrationThe mixture was concentrated on a rotary evaporator
  2. washwashed three times with saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. customdried under high vacuum
  6. custom590 mg (purity 89%, 95% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-68077e7a2250470697ad5c452dbfd821
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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