Ammonia → HCID 67326951, compound

HRID 1434884Notes

Reaction equation

HRID 1434884 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C@@:24]12[CH2:39][O:38][C@@H:26]([C@H:27]([N:29]3[CH:36]=[C:35]([CH3:37])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[O:28]1)[C@@H:25]2[OH:40])=[N+]=[N-].N>N1C=CC=CC=1>[NH2:20][CH2:23][C@@:24]12[CH2:39][O:38][C@@H:26]([C@H:27]([N:29]3[CH:36]=[C:35]([CH3:37])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[O:28]1)[C@@H:25]2[OH:40]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 91005463HCID 91005463, compound

Product 1

HCID 67326951HCID 67326951, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a nitrogen stream, triphenylphosphine (49 mg, 0.19 mmol) was added to a pyridine solution (3.0 ml) of Compound 4 (28 mg, 0.095 mmol), and the mixture was stirred for 3 hours at room temperature. A 28% aqueous solution of ammonia (5.0 ml) was added, and the mixture was stirred further for 14 hours. Then, the solvent was distilled off under reduced pressure to obtain 5′-amino-5′-deoxy-5-methyl-2′-O,4′-C-methyleneuridine (Compound 5) as a crude product.

Workup

  1. stirringthe mixture was stirred further for 14 hours
  2. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-14c33c95812c441f97a76d4bf60f2af0
Source dataset
uspto-grants-2009_11
Patent number
US07615619B2

Reaction notes

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