2-Amino-3-benzyloxypyridine → HCID 44594747, compound

HRID 1520431Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][C:19]([C:22](=O)[CH2:23][C:24](OCC)=[O:25])=[CH:18][CH:17]=1.C([O-])(=O)C.[NH4+]>O>[CH2:1]([O:8][C:9]1[C:10]2=[N:15][C:22]([C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)=[CH:23][C:24](=[O:25])[N:11]2[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of 5.02 mmol) of 3-(benzyloxy)pyridin-2-amine and 1.16 g (6.02 mmol) of ethyl 3-(4-pyridinyl)-3-oxopropionate were added 0.774 (10.04 mmol) of ammonium acetate. The reaction mixture was heated at 150° C. for 12 hours. After cooling, water was added and the mixture was extracted with dichloromethane. The extracts were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and evaporated. The residue obtained was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol n the proportions 99/1 to 90/10 to give 0.32 g (19%) of the desired compound which was transformed into the hydrochloride salt in the usual manner to give the pure product as a yellow solid.

Workup

temperatureAfter cooling
extractionthe mixture was extracted with dichloromethane
washThe extracts were washed with a saturated aqueous solution of sodium chloride
dry with materialdried over sodium sulphate
customevaporated
customThe residue obtained
customwas purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol n the proportions 99/1 to 90/10

Sources & evidence

ORD record: ord-5efd0f44253b46da838a833b93fc0943
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073915B2

Reaction notes

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