Sodium Methoxide → HCID 67050542, compound

HRID 2194809Notes

Reaction equation

HRID 2194809 reaction equation
[CH2:1]([N:5]1[C:10]([N:11]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=2)C(=O)C)=[C:9]([CH2:23][CH3:24])[C:8](=[O:25])[NH:7][C:6]1=[O:26])[CH:2]=[CH:3][CH3:4].C[O-].[Na+]>CO>[CH2:1]([N:5]1[C:10]([NH:11][C:15]2[CH:16]=[C:17]([CH3:22])[CH:18]=[C:19]([CH3:21])[CH:20]=2)=[C:9]([CH2:23][CH3:24])[C:8](=[O:25])[NH:7][C:6]1=[O:26])[CH:2]=[CH:3][CH3:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67050495HCID 67050495, compound

Product 1

HCID 67050542HCID 67050542, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(3-but-2-enyl-5-ethyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-N-(3,5-dimethyl-phenyl)-acetamide (110) (90 mg, 0.25 mmol) in methanol (3 mL), was added sodium methoxide (73 mg, 1.35 mmol). After 4 hr., the mixture was neutralized with excess. NH4Cl and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1)) to afford 57 mg (72%) of a white solid. m.p. 190-192° C.; 1H-NMR (200 MHz, CDCl3) δ 1.00 (3H, t, J=7.5 Hz), 1.68-1.70 (3H, m), 2.28-2.37 (8H, m), 4.31-4.33 (2H, m), 5.44 (1H, s), 5.51-5.58 (2H, m), 6.39 (2H, s), 6.66 (1H, s), 8.72 (1H, s); m/z (EI) 313 (M+).

Workup

  1. customNH4Cl and evaporated in vacuo
  2. customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1))

Sources & evidence

ORD record
ord-26575582577c4ecfba2e23a54afb297d
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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