Triphenylphosphine → HCID 68459531, compound

HRID 500644Notes

Reaction equation

HRID 500644 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.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH2:20]O)[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH2:20][CH2:19][CH2:18][C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)[N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 178613-PyridinepropanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178508725HCID 178508725, compound

Product 1

HCID 68459531HCID 68459531, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine, prepared as described in A. F. Burchat et al. Bioorg Med. Chem. Lett. 2002, 12, 1687-1690, (0.392 g, 1.5 mmol), 3-(pyridine-3-yl)propan-1-ol (0.388 ml, 3 mmol), and triphenylphosphine (0.983 g, 3.75 mmol) in THF (10 ml) under inert atmosphere was cooled in an ice bath and diisopropyl azodicarboxylate (0.581 ml, 3 mmol) was added dropwise and the reaction was then stirred for 72 hrs at ambient temperature. The reaction was concentrated and the residue was acidified with 1M HCl and washed with EtOAc. The aqueous layer was basified with solid Na2CO3 and extracted with EtOAc. The EtOAc was dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel using an ISCO Companion chromatography system eluted with 0-20% MeOH/CH2Cl2 to give the title compound as an off-white solid (310 mg, 54%). MS (ESI(+)) m/e 381 (M+H)+, (ESI(−)) m/e 379 (M−H)−; 1H NMR (300 MHz, DMSO-d6) 8.39 (m, 2H), 8.20 (s, 1H), 7.61 (dd, 1H), 7.28 (m, 1H), 4.19 (t, 2H), 2.60 (m, 2H), 2.17 (m, 2H).

Workup

  1. customprepared
  2. concentrationThe reaction was concentrated
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialThe EtOAc was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel using an ISCO Companion chromatography system
  9. washeluted with 0-20% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a111b0e3357045eebbae7d6c122c7811
Source dataset
uspto-grants-2010_08
Patent number
US07772231B2

Reaction notes

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