Triphenylphosphine → HCID 22055274, compound

HRID 1829929Notes

Reaction equation

HRID 1829929 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH2:7][OH:8].[NH2:9][C:10]1[CH:15]=[CH:14][C:13](O)=[C:12]([Cl:17])[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:17][C:12]1[CH:11]=[C:10]([NH2:9])[CH:15]=[CH:14][C:13]=1[O:8][CH2:7][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 775784-Amino-2-chlorophenolHCID 201734PyrazinemethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 22055274HCID 22055274, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of pyrazin-2-yl-methanol (62 mg, 0.56 mmol), 4-amino-2-chloro-phenol (80.8 mg, 0.56 mmol) and triphenylphosphine (148 mg, 0.56 mmol) in THF (3 ml) was added DIAD (0.11 ml, 0.56 mmol) and the mixture was stirred at rt for 20 h. The mixture was concentrated in vacuo, diluted with 1N HCl (30 ml), washed with EtOAc (3×20 ml) and basified to pH 12 by 1N NaOH. The mixture was extracted with EtOAc (4×40 ml) and the combined EtOAc extracts were washed with brine (1×20 ml), dried (MgSO4), filtered and concentrated in vacuo to give 16A (43.3 mg, 33% pure)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with 1N HCl (30 ml)
  3. washwashed with EtOAc (3×20 ml)
  4. extractionThe mixture was extracted with EtOAc (4×40 ml)
  5. washthe combined EtOAc extracts were washed with brine (1×20 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e4a286337d745329c8a38ca55066594
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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