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

HRID 1593443
Notes
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Reaction equation

HRID 1593443 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 286947Carbonic acid-guanidine (1:1)HCID 865954205-[2-((E)-3-Dimethylaminoallanoyl)furan-3-yl]indan-1-one O-methyloxime

Product 1

HCID 865954215-[2-(2-Aminopyrimidin-4-yl)furan-3-yl]indan-1-one O-methyloximeYield 67.1%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
2×
HCID 312751,4-DioxaneSolvent

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

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture extracted into ethyl acetate (2×)
  3. washwashed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with dichloromethane
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes