Triethylamine → HCID 178432595, compound

HRID 570529Notes

Reaction equation

HRID 570529 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15](=[NH:17])[NH2:16])=[N:6]1.C([N:24](CC)CC)C.O.NN>C(O)C>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15](=[NH:16])[NH:17][NH2:24])=[N:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 866920951-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide

Product 1

HCID 178432595HCID 178432595, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

688 mg (approx. 2.20 mmol, purity 92%) of 1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide were initially charged in 10 ml of ethanol and cooled to 0° C. 891 mg (8.80 mmol) of triethylamine and 138 mg (2.20 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. 654 mg (purity 93%, 92% 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. custom654 mg (purity 93%, 92% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-a71385612d534bf89fc370d764342cce
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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