Dimethylformamide → HCID 25215197, compound

HRID 2194789Notes

Reaction equation

HRID 2194789 reaction equation
[CH:1]([C:4]1[C:5](=[O:21])[NH:6][C:7](=O)[NH:8][C:9]=1[C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH3:3])[CH3:2].[C:22](=[O:25])([O-])[O-].[K+].[K+].[CH3:28]N(C=O)C>>[CH2:7]([N:8]1[C:9]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:21])[NH:6][C:22]1=[O:25])[CH3:28]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 67050506HCID 67050506, compound

Product 1

HCID 25215197HCID 25215197, compoundYield 23%

Procedure

5-Isopropyl-6-quinolin-3-yl-1H-pyrimidine-2,4-dione (6 mg, 0.021 mmol, 1.0 eq.) was dissolved in 0.5 mL DMF. Potassium carbonate (3 mg, 1 eq.) was added and the reaction mixture was stirred at room temperature for 10 minutes. Ed (1.7 μL, 1 eq.) was added. The reaction mixture was stirred at room temperature overnight. No reaction was observed. More potassium carbonate (6 mg) was added. The reaction mixture was complete after 2 hours. The reaction crude was filtered and purified by reverse phase HPLC to give a white powder (1.5 mg, 23%). LC-MS shows 310.2 (M+1). 1H-NMR (300 MHz, CDCl3): δ 8.83 (s, 1H), 8.40 (m, 1H), 8.22 (m, 1H), 7.96 (m, 2H), 7.78 (m, 1H), 3.58 (m, 2H), 2.10 (m, 1H), 1.90 (dd, 6H), 1.04 (t, 3H).

Workup

  1. additionEd (1.7 μL, 1 eq.) was added
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. waitThe reaction mixture was complete after 2 hours
  4. customThe reaction crude
  5. filtrationwas filtered
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-d969c115d75845df84bcef962bb9e0ee
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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