Ammonium formate → [2-(5-Amino-4-methoxy-pyrimidin-2-yloxy)-ethyl]-propyl-carbamic Acid Tert-Butyl Ester

HRID 390294Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:11][CH2:12][O:13][C:14]1[N:19]=[C:18]([O:20][CH3:21])[C:17]([N+:22]([O-])=O)=[CH:16][N:15]=1)[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].O>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:11][CH2:12][O:13][C:14]1[N:19]=[C:18]([O:20][CH3:21])[C:17]([NH2:22])=[CH:16][N:15]=1)[CH2:8][CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of crude [2-(4-methoxy-5-nitro-pyrimidin-2-yloxy)-ethyl]-propyl-carbamic acid tert-butyl ester (1.76 g, 4.94 mmol) and 10% palladium on charcoal (200 mg) in water (15 ml) was slowly added a solution of ammonium formate (3.12 g, 49.44 mmol) in water (10 ml) at 80° C. After stirring for 1 h at 80° C. the mixture was filtered and concentrated under reduced pressure. The aqueous layer was extracted three times with dichloromethane. The combined organic layers were dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography with toluene/THF/MeOH (4:1:1)/2.5% triethylamine to give 720 mg (44.7%) of the title compound.

Workup

filtrationwas filtered
concentrationconcentrated under reduced pressure
extractionThe aqueous layer was extracted three times with dichloromethane
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography with toluene/THF/MeOH (4:1:1)/2.5% triethylamine

Sources & evidence

ORD record: ord-f404ad405acb44e8819cffafed0fc042
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383641B2

Reaction notes

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