Triphenylphosphine → HCID 86711292, compound

HRID 336159Notes

Reaction equation

HRID 336159 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:35][C@@H:36]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:37]=[CH2:38].[Cl:47][C:48]1[C:49]2[C:56]([I:57])=[CH:55][NH:54][C:50]=2[N:51]=[CH:52][N:53]=1>O1CCCC1>[Cl:47][C:48]1[C:49]2[C:56]([I:57])=[CH:55][N:54]([CH2:35][C@@H:36]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:37]=[CH2:38])[C:50]=2[N:51]=[CH:52][N:53]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11041481(S)-tert-butyl 1-hydroxybut-3-en-2-ylcarbamateHCID 148092816-Chloro-7-iodo-7-deazapurine

Product 1

HCID 86711292HCID 86711292, compoundYield 186.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropyl azodicarboxylate (2.44 ml) was slowly added to a solution of triphenylphosphine (13.1 g) in tetrahydrofuran (70 ml) under ice-cooling. The reaction mixture was stirred under ice-cooling for 1 hour, and then a solution of (S)-tert-butyl (1-hydroxybut-3-en-2-yl)carbamate (7.0 g) synthesized according to the method disclosed in Non-patent Literature Org. Lett., 2005, vol. 7, No. 5, pp. 847-849 and 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (6.97 g) in tetrahydrofuran (35 ml) was slowly added thereto. After the reaction mixture was stirred at room temperature for 2 hours, the solvent was 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 (20.84 g) as a light-yellow, oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. stirringAfter the reaction mixture was stirred at room temperature for 2 hours
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3c7bed2d2f3f4bd8a2659651c9615845
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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