Ammonium Chloride → HCID 67050507, compound

HRID 2194806Notes

Reaction equation

HRID 2194806 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]([CH:23]([CH3:25])[CH3:24])[C:8](=[O:26])[NH:7][C:6]1=[O:27])[CH:2]=[CH:3][CH3:4].C[O-].[Na+].[NH4+].[Cl-]>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]([CH:23]([CH3:24])[CH3:25])[C:8](=[O:26])[NH:7][C:6]1=[O:27])[CH:2]=[CH:3][CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 67050494HCID 67050494, compound

Product 1

HCID 67050507HCID 67050507, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(3-but-2-enyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-N-(3,5-dimethyl-phenyl)-acetamide (107) (100 mg, 0.27 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 (1:2)) to afford 62 mg (70%) of a white solid. m.p. 186-187° C.; 1H-NMR (200 MHz, CDCl3) δ 1.17 (6H, d, J=6.9 Hz), 1.64-1.67 (3H, m), 2.24 (6H, s), 2.86 (1H, m), 4.25-4.30 (2H, m), 5.33 (1H, s), 5.48-5.54 (2H, m), 6.32 (2H, s), 6.60 (1H, s), 8.42 (1H, s); m/z (EI) 327 (M+).

Workup

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

Sources & evidence

ORD record
ord-b36d39a68af849628c8961e7d1c9d90a
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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