Barbituric Acid → HCID 7298503, compound

HRID 1271913Notes

Reaction equation

HRID 1271913 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=2[CH:11]=O)[CH2:3]1.[NH:20]1[C:27](=[O:28])[CH2:26][C:24](=[O:25])[NH:23][C:21]1=[O:22]>CO>[CH3:1][C@@H:2]1[O:7][C@@H:6]([CH3:8])[C@@H:5]2[C:26]3([CH2:11][C:10]4[C:9]([N:4]2[CH2:3]1)=[CH:16][CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=4)[C:24](=[O:25])[NH:23][C:21](=[O:22])[NH:20][C:27]3=[O:28]

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 58847022HCID 58847022, compound

Product 1

HCID 7298503HCID 7298503, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

2-[(2S,6S)-2,6-Dimethylmorpholin-4-yl]-5-nitrobenzaldehyde (298 mg, 1.12 mmol) is combined with barbituric acid (159 mg, 1.12 mmol, Aldrich) in a vial with MeOH (2 mL). The sealed reaction is heated to 60° C. on a shaker block for 21 hours and then the solvent is evaporated. The product is purified on a Biotage Flash 40M+ using a 1:1 mixture of EtOAc and toluene as eluent Product is dried under vacuum yielding a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.91, 1.24, 2.91, 3.56, 3.63, 3.83–3.91, 3.95, 4.07, 4.14–4.24, 6.85, 7.83, 7.98, 11.59, 11.89.

Workup

  1. customThe sealed reaction
  2. customthe solvent is evaporated
  3. customThe product is purified on a Biotage Flash 40M+
  4. additiona 1:1 mixture of EtOAc and toluene as eluent Product
  5. customis dried under vacuum
  6. customyielding a yellow-orange solid

Sources & evidence

ORD record
ord-a80bf99b13a0465189a19eb078ba445e
Source dataset
uspto-grants-2007_04
Patent number
US07208490B2

Reaction notes

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