Formaldehyde → HCID 22106143, compound

HRID 1456400Notes

Reaction equation

HRID 1456400 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]#[CH:24])[CH:16]=2)=[C:7]([NH:25][C:26]([NH:28][C:29]2[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=2[CH:38]([CH3:40])[CH3:39])=[O:27])[C:6]1=[O:41])[CH2:2][CH2:3][CH3:4].C=O.[CH2:44]([NH:46][CH2:47][CH3:48])[CH3:45].[CH3:49]COCC>O1CCOCC1.[Cu]I>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]#[C:24][CH2:49][N:46]([CH2:47][CH3:48])[CH2:44][CH3:45])[CH:16]=2)=[C:7]([NH:25][C:26]([NH:28][C:29]2[C:30]([CH:38]([CH3:40])[CH3:39])=[CH:31][CH:32]=[CH:33][C:34]=2[CH:35]([CH3:36])[CH3:37])=[O:27])[C:6]1=[O:41])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 8021DiethylamineHCID 22106381HCID 22106381, compound

Product 1

HCID 22106143HCID 22106143, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-[1-butyl-4-{3-(2-propynyloxy)phenyl}-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (1.0 g, 1.82 mmol) in dioxane (10 ml) were added paraformaldehyde (0.37 g), diethylamine (0.26 g, 3.63 mmol) and copper (I) iodide, and the mixture was stirred at room temperature for two hours. To the mixture was added ether, and the mixture was filtered through a cerite pad. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (2% methanol in chloroform) to give the title compound (1.05 g, 1.65 mmol).

Workup

  1. filtrationthe mixture was filtered through a cerite pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (2% methanol in chloroform)

Sources & evidence

ORD record
ord-2da4e8d7eb1e47438c125237e2b2157d
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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