Triphenylphosphine → HCID 22346849, compound

HRID 898025Notes

Reaction equation

HRID 898025 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[CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH:17]3[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16]3)[N:3]=[C:2]([I:1])[C:10]=12

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinolHCID 5462977Diethyl azodicarboxylateHCID 178508725HCID 178508725, compound

Product 1

HCID 22346849HCID 22346849, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (5.0 g, 19.15 mmol) in tetrahydrofuran (100 mL) was treated with tert-butyl 3-hydroxy-1-pyrrolidinecarboxylate (5.38 g, 28.73 mmol) and triphenylphosphine (7.53 g, 28.73 mmol). The reaction mixture was cooled to 0° C. on an ice bath. Diethylazodicarboxyate (5.0 g, 28.73 mmol) was slowly added to the reaction mixture. The solvent was removed under reduced pressure after 6 days. The crude oil was used directly in the subsequent reaction without further analysis.

Workup

  1. customThe solvent was removed under reduced pressure after 6 days
  2. customThe crude oil was used directly in the subsequent reaction without further analysis

Sources & evidence

ORD record
ord-f4ea999eff7e4b00b7582e700ec89158
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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