Lithium hydroxide, monohydrate → (+)-6-(Azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid

HRID 1868487Notes

Reaction equation

[N:1]([CH2:4][C:5]1[C:6]([CH3:27])=[N:7][C:8]2[N:9]([CH:19]=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[N+:2]=[N-:3].O[Li].O>C1COCC1.O>[N:1]([CH2:4][C:5]1[C:6]([CH3:27])=[N:7][C:8]2[N:9]([CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (+)-ethyl 6-(azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (1 g, 2.47 mmol) in THF (20 mL) and H2O (2 mL) was added LiOH.H2O (155 mg, 3.70 mmol). After heating to 50° C. for 16 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The aqueous layer was acidified by 1N HCl to pH=1. The organic layer was washed with satd aq NH4Cl and brine before drying over MgSO4. Filtration, concentration under reduced pressure provided (+)-6-(azidomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid (874 mg, 94%) as a white solid.

Workup

concentrationthe reaction was concentrated under reduced pressure
additiondiluted with EtOAc
washThe organic layer was washed with satd aq NH4Cl and brine
dry with materialbefore drying over MgSO4
filtrationFiltration, concentration under reduced pressure

Sources & evidence

ORD record: ord-2ad21cf2df844537bc6bce73311aa874
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635699B2

Reaction notes

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