Barbituric Acid → HCID 58847031, compound

HRID 1271910Notes

Reaction equation

HRID 1271910 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH2:8][CH2:9][CH3:10])[CH2:5][N:4]([C:11]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:12]=2[CH:13]=O)[CH2:3]1.[NH:22]1[C:29](=[O:30])[CH2:28][C:26](=[O:27])[NH:25][C:23]1=[O:24]>CO>[CH3:1][C@H:2]1[C@@H:3]2[C:28]3([CH2:13][C:12]4[C:11]([N:4]2[CH2:5][C@@H:6]([CH2:8][CH2:9][CH3:10])[O:7]1)=[CH:18][CH:17]=[C:16]([N+:19]([O-:21])=[O:20])[CH:15]=4)[C:26](=[O:27])[NH:25][C:23](=[O:24])[NH:22][C:29]3=[O:30]

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 131726347HCID 131726347, compound

Product 1

HCID 58847031HCID 58847031, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

2-(cis-2-methyl-6-propylmorpholin-4-yl)-5-nitrobenzaldehyde (446 mg, 1.53 mol) is combined with barbituric acid (217 mg, 1.53 mmol, Aldrich) in a vial with MeOH (6 mL). The sealed reaction is heated to 80° C. on a shaker block for 19 hours and then the solvent is removed by rotary evaporation. The product is purified 2× on a Biotage Flash 75M using 10% MTBE in CH2Cl2 eluent. The product is dried under vacuum at 100° C. yielding a yellow-orange solid. 1H NMR (400 MHz, ACETONITRILE-D3) δ ppm 0.95, 1.00, 1.47, 3.04, 3.34, 3.56, 3.95, 4.14, 6.85, 7.77, 8.02, 9.19.

Workup

  1. customThe sealed reaction
  2. customthe solvent is removed by rotary evaporation
  3. customThe product is purified 2× on a Biotage Flash 75M
  4. customThe product is dried under vacuum at 100° C.
  5. customyielding a yellow-orange solid

Sources & evidence

ORD record
ord-1ce27346df2143648a3d86f398fe6b6d
Source dataset
uspto-grants-2007_04
Patent number
US07208490B2

Reaction notes

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