Water → HCID 68694313, compound

HRID 2236911Notes

Reaction equation

HRID 2236911 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[C:7](=[O:16])[CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][N:8]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[C:7](=[O:16])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86619605HCID 86619605, compound

Product 1

HCID 68694313HCID 68694313, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 4-azidomethyl-1-thiophen-3-yl-1H-pyridin-2-one in tetrahydrofuran (2 mL) is added triphenylphosphine (0.19 g). The mixture is stirred for 10 minutes before the addition of water (200 μL). After stirring for 16 hours at room temperature, the mixture is purified by reverse-phase high performance liquid chromatography (5% acetonitrile/95% water to 75% acetonitrile/25% water over 45 minutes) to provide 4-aminomethyl-1-thiophen-3-yl-1H-pyridin-2-one (60 mg, 34% over 2 steps).

Workup

  1. customthe mixture is purified by reverse-phase high performance liquid chromatography (5% acetonitrile/95% water to 75% acetonitrile/25% water over 45 minutes)

Sources & evidence

ORD record
ord-cb9a14d7f7104154b5b8e76d9f8158a3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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