Butyl iodide → HCID 58203434, compound

HRID 2194804Notes

Reaction equation

HRID 2194804 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([C:10]1[C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12][C:11]=1[O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[C:22]#[N:23])([CH3:9])[CH3:8].[CH2:28](I)[CH2:29][CH2:30][CH3:31]>CN(C=O)C>[CH2:28]([N:12]1[C:11]([O:18][C:19]2[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=2)[C:22]#[N:23])=[C:10]([CH:7]([CH3:9])[CH3:8])[C:15](=[O:16])[NH:14][C:13]1=[O:17])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 596868373-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrile

Product 1

HCID 58203434HCID 58203434, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (9.3 mg, 0.0067 mmol, 1.0 eq.) was added to 3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrile (103) (23 mg, 0.0.08 mmol, 1.2 eq.) in 1.0 mL DMF. The reaction mixture was stirred at room temperature for 10 minutes, and n-butyl iodide (7.6 μL, 0.0.067 mmol) was added. The reaction mixture was filtered and purified by reverse phase HPLC (MeCN/water) to give a white powder (3.8 mg, 17%). LC-MS shows 342.1 (M+1). 1H NMR (300 MHz, CDCl3): δ 8.37 (br, 1H), 7.28 (s, 1H), 7.08 (s, 1H), 6.98 (s, 1H), 3.42 (t, 2H), 2.71 (m, 1H), 2.42 (s, 3H), 1.60 (m, 2H), 1.28 (m, 2H), 1.17 (d, 6H), 0.88 (t, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse phase HPLC (MeCN/water)

Sources & evidence

ORD record
ord-2d6f0191176746d6bb5d0ddb00c5ba24
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

Loading…