Triphenylphosphine → HCID 86711286, compound

HRID 336151Notes

Reaction equation

HRID 336151 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[C:22]2[C:29]([I:30])=[CH:28][NH:27][C:23]=2[N:24]=[CH:25][N:26]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[CH2:46][CH2:47][C@@H:48]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH:49]=[CH2:50]>COCCOC>[Cl:20][C:21]1[C:22]2[C:29]([I:30])=[CH:28][N:27]([CH2:50][CH2:49][C@@H:48]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH:47]=[CH2:46])[C:23]=2[N:24]=[CH:25][N:26]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 148092816-Chloro-7-iodo-7-deazapurineHCID 15274845HCID 15274845, compound

Product 1

HCID 86711286HCID 86711286, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Triphenylphosphine (3.25 g) was added to and dissolved in a solution of (R)-tert-butyl (5-hydroxypent-1-en-3-yl)carbamate (2.5 g) obtained in Step 3 and 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (2.31 g) obtained in Step 1 of Example 1 in DME (23 ml) under ice-cooling. Thereafter, diisopropyl azodicarboxylate (2.44 ml) was gradually added thereto. The reaction mixture was stirred under ice-cooling for 30 minutes and at room temperature for 1 hour, and the solvent was then distilled off under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a light-yellow solid (3.49 g).

Workup

  1. temperaturecooling
  2. distillationthe solvent was then distilled off under reduced pressure
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7d9b3165c8244df8a259620472428bc1
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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