Trifluoroacetic acid methylene chloride → 3-Iodo-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432284Notes

Reaction equation

HRID 432284 reaction equation
FC(F)(F)C(O)=O.ClCCl.[NH2:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]2[N:18]([CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[N:19]=[C:20]([I:21])[C:13]=12>ClCCl>[I:21][C:20]1[C:13]2[C:14](=[N:15][CH:16]=[N:17][C:12]=2[NH2:11])[N:18]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[N:19]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 22346822tert-Butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 223466933-Iodo-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trifluoroacetic acid/dichloromethane (20:80, 250 mL) was added to a solution of tert-butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (10.72 g, 24.1 mmol) in dichloromethane (100 mL) at 0° C. 15 minutes later, the ice-bath was removed and the reaction mixture was stirred at room temperature for 5 hours. The solvents were evaporated and the residue was dissolved in dichloromethane. Hydrochloric acid (5.0N) was added and the aqueous layer was washed with dichloromethane three times. Sodium hydroxide (50%) was added to adjust the pH to about 10. The suspension was lyophilized to reduce the volume to one third of the original volume. The solid was collect by filtration to give 3-iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (8.109 g, 97%). 1H NMR (CDCl3) δ 1.81 (m, 2H), 1.99 (m, 2H), 2.65 (m, 2H), 3.07 (m, 2H), 4.68 (m, 1H), 8.19 (s, 1H).

Workup

  1. custom15 minutes later, the ice-bath was removed
  2. customThe solvents were evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additionHydrochloric acid (5.0N) was added
  5. washthe aqueous layer was washed with dichloromethane three times
  6. additionSodium hydroxide (50%) was added
  7. filtrationThe solid was collect by filtration

Sources & evidence

ORD record
ord-9ec091ece6314a78bbf5a9d2506e4588
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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