Sodium Hydroxide → 5-[2-(2-Aminopyrimidin-4-yl)furan-3-yl]indan-1-one O-methyloxime

HRID 1593443Notes

Reaction equation

[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:17]=[CH:16][O:15][C:14]=3[C:18](=O)/[CH:19]=[CH:20]/N(C)C)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.C(=O)(O)O.[NH2:29][C:30]([NH2:32])=[NH:31].[OH-].[Na+]>O1CCOCC1.O>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:17]=[CH:16][O:15][C:14]=3[C:18]3[CH:19]=[CH:20][N:29]=[C:30]([NH2:32])[N:31]=3)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of the product of Step 2 (0.30 g, 0.93 mmol) in 1,4dioxane (6 ml) was treated with a solution of guanidine carbonate (0.33 g, 1.86 mmol) and sodium hydroxide (0.1 7 g, 4.1 mmol) in water (2 ml). The mixture was heated at 100° C. for 4 hours. After cooling to room temperature, water was added and the mixture extracted into ethyl acetate (2×). The organic layers were combined and washed with saturated brine, dried (MgSO4) and concentrated in vacuo. The residue was triturated with dichloromethane and the resulting solid filtered to afford the title compound (200 mg, 67%); MS(ES+) m/e 321 [M+H]+.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture extracted into ethyl acetate (2×)
washwashed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was triturated with dichloromethane
filtrationthe resulting solid filtered

Sources & evidence

ORD record: ord-afed46a8a9b44052bcf45ff4a2742ff3
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07297694B2

Reaction notes

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