Triphenylphosphine → HCID 86594457, compound

HRID 1797433Notes

Reaction equation

HRID 1797433 reaction equation
[CH3:1][C:2]([Si:5]([CH3:24])([CH3:23])[O:6][CH:7]1[CH2:11][CH:10](O)[C:9](=[CH2:13])[CH:8]1[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])([CH3:4])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:44][C:45]1[N:53]=[C:52]2[C:48]([NH:49][CH:50]=[N:51]2)=[C:47]([Cl:54])[N:46]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(Cl)Cl>[Cl:54][C:47]1[N:46]=[C:45]([NH2:44])[N:53]=[C:52]2[C:48]=1[N:49]=[CH:50][N:51]2[CH:10]1[CH2:11][CH:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:8]([CH2:7][O:6][Si:5]([C:2]([CH3:4])([CH3:1])[CH3:3])([CH3:24])[CH3:23])[C:9]1=[CH2:13]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53603492-Amino-6-chloropurineHCID 76386712HCID 76386712, compound

Product 1

HCID 86594457HCID 86594457, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a suspension of 56 (120 mg, 0.32 mmol), triphenylphosphine (84.5 mg, 0.64 mmol), and 2-amino-6-chloropurine (108 mg, 0.64 mmol) in THF (10 mL) was added diethyl azodicarboxylate (111 mg, 0.64 mmol) at −20° C. The reaction mixture was stirred at −20° C. for 1 hour. It was poured into DCM (50 mL), washed with 0.5 N sodium hydroxide (3×10 mL), dried over sodium sulfate, and concentrated in vacuo. Purification via silica gel chromatography gave the title compound (0.11 g, 63%).

Workup

  1. washwashed with 0.5 N sodium hydroxide (3×10 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-835f5e65a8e143eebb662a7328e810d4
Source dataset
uspto-grants-2006_04
Patent number
US07034152B2

Reaction notes

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