Triphenylphosphine → tert-butyl (S)-3-(4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

HRID 898042Notes

Reaction equation

HRID 898042 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.O[C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([C@H:17]3[CH2:18][CH2:13][CH2:14][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]3)[N:3]=[C:2]([I:1])[C:10]=12

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 1514398(R)-1-Boc-3-hydroxypiperidine2×HCID 178508725HCID 178508725, compound

Product 1

HCID 69204686tert-butyl (S)-3-(4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2 g, 0.0077 mol), (R)-tert-butyl 3-hydroxy-1-piperidinecarboxylate (2.3 g, 0.012 mol), and triphenylphosphine (3 g, 0.012 mol) in tetrahydrofuran (70 mL), diethyl azodicarboxylate (2 g, 0.012 mol) was added at 0° C. The mixture was stirred at room temperature under an atmosphere of nitrogen for 2 days. In order to complete the reaction, additional (R)-tert-butyl 3-hydroxy-1-piperidinecarboxylate (0.62 g, 0.003 mol), and triphenylphosphine (0.81 g, 0.012 mol), and diethyl azodicarboxylate (0.6 g, 0.003 mol) were added to the mixture. The mixture was stirred at room temperature under an atmosphere of nitrogen for additional 18 hours. The solvent was removed under the reduced pressure to yield crude (S)-tert-butyl 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate, which was used crude for the next reaction.

Workup

  1. additionwas added at 0° C
  2. additionwere added to the mixture
  3. stirringThe mixture was stirred at room temperature under an atmosphere of nitrogen for additional 18 hours
  4. customThe solvent was removed under the reduced pressure

Sources & evidence

ORD record
ord-ddd0bac9669148c899c9b0ae176a0209
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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