Barbituric Acid → HCID 18455554, compound

HRID 1820643Notes

Reaction equation

HRID 1820643 reaction equation
[Br:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]=O)=[C:4]([N:13]2[CH2:18][CH:17]([CH3:19])[O:16][CH:15]([CH3:20])[CH2:14]2)[CH:3]=1.[NH:21]1[C:28](=[O:29])[CH2:27][C:25](=[O:26])[NH:24][C:22]1=[O:23]>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:6][C:27]3([CH:14]4[CH:15]([CH3:20])[O:16][CH:17]([CH3:19])[CH2:18][N:13]42)[C:25](=[O:26])[NH:24][C:22](=[O:23])[NH:21][C:28]3=[O:29])=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 18455594HCID 18455594, compound

Product 1

HCID 18455554HCID 18455554, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-bromo-2-(2,6-dimethylmorpholin-4-yl)-5-nitrobenzaldehyde (from Step 2) (989 mg, 2.88 mmol) and barbituric acid (369 mg, 2.88 mmol) in isopropanol (15 mL) is sealed in a 20 mL scintillation vial and shaken at 85° C. for 2.5 hours. The product is adsorbed onto silica gel and purified by silica gel chromatography using a gradient from 20% EtOAc in CH2Cl2 to 25% EtOAc in CH2Cl2 as eluent. Product is isolated and dried (20 Torr, 100° C.) to give 512 mg of yellow solid. 1H NMR (DMSO-d6) δ 11.90, 11.62, 7.79, 7.36, 4.32, 3.87, 3.47-3.63, 2.94, 2.81, 1.15, 0.94.

Workup

  1. customis sealed in a 20 mL scintillation vial
  2. custompurified by silica gel chromatography
  3. customProduct is isolated
  4. customdried (20 Torr, 100° C.)

Sources & evidence

ORD record
ord-150028dc7405419c9e5c115e58fe5069
Source dataset
uspto-grants-2009_10
Patent number
US07605157B2

Reaction notes

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