Barbituric Acid → HCID 7298503, compound

HRID 1820659Notes

Reaction equation

HRID 1820659 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-4fb547cc22d046019c7fc54ca2e2c078
Source dataset
uspto-grants-2009_10
Patent number
US07605157B2

Reaction notes

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